CN102603467A - Preparation method of propyldicyclohexyl bromide - Google Patents
Preparation method of propyldicyclohexyl bromide Download PDFInfo
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- CN102603467A CN102603467A CN201210032757XA CN201210032757A CN102603467A CN 102603467 A CN102603467 A CN 102603467A CN 201210032757X A CN201210032757X A CN 201210032757XA CN 201210032757 A CN201210032757 A CN 201210032757A CN 102603467 A CN102603467 A CN 102603467A
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- propyl group
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- group dicyclohexyl
- bromine
- reaction
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 title abstract 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000002994 raw material Substances 0.000 claims abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005893 bromination reaction Methods 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 58
- -1 dicyclohexyl bromine Chemical compound 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000000967 suction filtration Methods 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 14
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000006722 reduction reaction Methods 0.000 claims description 9
- 230000000630 rising effect Effects 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- TWXWPPKDQOWNSX-UHFFFAOYSA-N dicyclohexylmethanone Chemical compound C1CCCCC1C(=O)C1CCCCC1 TWXWPPKDQOWNSX-UHFFFAOYSA-N 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 238000007710 freezing Methods 0.000 claims description 6
- 230000008014 freezing Effects 0.000 claims description 6
- 238000010025 steaming Methods 0.000 claims description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000284 extract Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 3
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 16
- 239000004973 liquid crystal related substance Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010907 mechanical stirring Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000013019 agitation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 238000007867 post-reaction treatment Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000001780 epistaxis Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 208000011309 nasal bleeding Diseases 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of propyldicyclohexyl bromide, which comprises the following steps: reducing propyldicyclohexyl ketone as a raw material with sodium borohydride as a reducing agent to obtain a reduction product of propyldicyclohexyl alcohol, carrying out a bromination reaction of the propyldicyclohexyl alcohol under an action of hydrobromic acid to generate liquid-state propyldicyclohexyl bromide, and carrying out subsequent treatment to obtain solid-state propyldicyclohexyl bromide. Compared with the well-known preparation methods of ethyldicyclohexyl bromide, the preparation method of propyldicyclohexyl bromide disclosed by the invention does not use triphenylphosphine, is simple and convenient in the subsequent treatment, and reduces the degree of environmental pollution. The hazard index of hydrobromic acid used in the preparation method disclosed by the invention is far lower than that of bromine used in the well-known preparation methods of ethyldicyclohexyl bromide so as to increase the safety factor. In addition, hydrobromic acid used in the preparation method disclosed by the invention can be recycled so as to reduce the production cost, and the preparation method lays the foundation for large-scale industrial production of propyldicyclohexyl bromide.
Description
Technical field
The present invention relates to a kind of liquid crystal display material, particularly a kind of TFT (thin film transistor) mode liquid crystal shows the preparation method of midbody propyl group dicyclohexyl bromine.
Background technology
Liquid crystal material is a kind of macromolecular material, and because of its special physics, chemistry, optical characteristics, 20 middle of century begin to be widely used on the technique of display of light and thin type.In recent years liquid crystal material develops rapidly along with the development of indicating meter, shows that wherein using to the row material is one type of liquid crystal material with fastest developing speed, that the market occupancy volume is maximum.
Nematic liquid crystal shows the liquid-crystal display of TN (twisted-nematic phase) pattern, STN (supertwist nematic phase) pattern, TFT (thin film transistor) pattern.Wherein propyl group dicyclohexyl bromine is a kind of important intermediate that the TFT mode liquid crystal shows, in liquid crystal material synthetic, plays important effect.Especially be applied to TFT (thin film transistor), LCD (liquid crystal display) field of liquid crystals.
Through retrieval, U.S. US6716491; (2004) a kind of preparation method of ethyl dicyclohexyl bromine is disclosed; Concrete operation steps is following: earlier triphenylphosphine and acetonitrile are dropped in the reaction flask, temperature control drips bromine in the time of 5～15 ℃ then; Dropwise in two hours; In the time of 5 ℃, mix subsequently and stirred one hour, add ethyl dicyclohexyl alcohol, the product of generation is an ethyl dicyclohexyl bromine.This preparing method's shortcoming is that the triphenylphosphine that adds in the reaction deals with very difficulty, and processing cost is high, and if deal with improperly also and can cause certain harm environment; In addition, used bromine among this preparation method, its hazard index is higher, and liquid bromine has cauterization effect to skin, and bromine vapor is prone to the mucous membrane of burning, and symptoms such as cough, mucous membrane secretory product increase, nasal bleeding, dizziness occur.
Summary of the invention
The object of the present invention is to provide a kind of TFT (thin film transistor) mode liquid crystal to show the preparation method of midbody propyl group dicyclohexyl bromine; The post-reaction treatment of present method is easy; Environmental pollution is little, and the hazard index of agents useful for same is low, and can recycling to reduce production costs.
Technical scheme of the present invention is following:
The preparation method of propyl group dicyclohexyl bromine is characterized in that, may further comprise the steps:
(1) propyl group dicyclohexyl ketone and Peng Qinghuana generation reduction reaction make propyl group dicyclohexyl alcohol,
Wherein, said solvent is one or more mixtures in water, THF, ethanol or the methyl alcohol,
(2) with the above-mentioned propyl group dicyclohexyl alcohol and Hydrogen bromide generation bromination reaction that makes, resultant of reaction extracts, revolves steaming through separatory and obtains liquid propyl group dicyclohexyl bromine,
(3) the above-mentioned liquid propyl group dicyclohexyl bromine that makes is obtained the solid-state propyl group dicyclohexyl of white powder bromine through freezing, suction filtration, temperature rising reflux, stirring cooling, suction filtration.
The temperature of reaction of reduction reaction is 0 ℃-110 ℃ in the said step (1), is preferably 10 ℃-60 ℃.
Reduction reaction in the said step (1), the mol ratio of propyl group dicyclohexyl ketone and Peng Qinghuana is 1 ︰ (0.1～5), is preferably 1 ︰ (0.1～2).
The temperature of reaction of bromination reaction is 90 ℃-150 ℃ in the said step (2), is preferably 100 ℃-120 ℃.
Bromination reaction in the said step (2), propyl group dicyclohexyl alcohol is 1 ︰ (3～20) with hydrobromic mol ratio, is preferably 1 ︰ (3～10).
Said step (1) reduction reaction resultant through suction filtration, wash, drain after as the raw material of step (2) bromination reaction.
Temperature rising reflux reflux state occurs more than being meant and adding ethanol and be warming up to the ethanol boiling point in the said step (3).
Beneficial effect of the present invention: the present invention is raw material, is reductive agent generation reduction reaction with the Peng Qinghuana with propyl group dicyclohexyl ketone; Obtain reduzate propyl group dicyclohexyl alcohol; Bromination reaction takes place and generates liquid propyl group dicyclohexyl bromine in propyl group dicyclohexyl alcohol under hydrobromic effect, handle obtaining solid-state propyl group dicyclohexyl bromine through postorder; Compare with known ethyl dicyclohexyl bromine preparation method, do not use triphenylphosphine in the reaction, post-reaction treatment is easy, has reduced the pollution level to environment; Used hydrobromic hazard index has improved SF far below used bromine among the known ethyl dicyclohexyl bromine preparation method among the present invention; In addition, used Hydrogen bromide can recycling among the present invention, has reduced production cost, for the large-scale industrial production of propyl group dicyclohexyl bromine is laid a good foundation.
Embodiment
Below in conjunction with embodiment the present invention is done further explain.
Embodiment 1
Add entry 27.8mol water, Peng Qinghuana 0.26mol (0.5eq) in three mouthfuls of reaction flasks of 1000ml; After treating that Peng Qinghuana dissolves fully under stirring; At room temperature slowly drip propyl group dicyclohexyl 0.518mol (1.0eq), react at 20 ℃ then, the question response system presents more white powder time point plate and confirms to have or not raw material; If do not have, then explanation reacts completely.Resultant of reaction is behind suction filtration, and with the saturated sodium bicarbonate solution washing, and then with clear water washing 3～4 times, through draining, dry the propyl group dicyclohexyl alcohol 0.58mol that obtains water ratio 16%, yield is used for next step bromination reaction greater than 95%.Put up mechanical stirring device, add above-mentioned propyl group dicyclohexyl alcohol 0.067mol (1.0eq), add Hydrogen bromide 0.67mol (10eq) temperature rising reflux then at the there-necked flask of 250ml; Reflux temperature is 120 ℃; Observing response system clear, no white powder raw material takes a plate or survey GC to carry out middle control this moment; Check to have or not raw material, until reacting completely.The mode of adopt the separatory extraction, revolving steaming obtains liquid propyl group dicyclohexyl bromine 0.0453mol, and content is about 90%, yield about 86.7%.The liquid propyl group dicyclohexyl bromine that obtains is put into freezing in the refrigerator-freezer (temperature is subzero 20 degrees centigrade); Have solid to separate out, suction filtration obtains little yellow solid, and ethanol adds the back temperature rising reflux by 5 times equivalent; After treating that solid dissolves fully; Naturally stir cooling, solid is separated out subsequently, obtains the solid-state propyl group dicyclohexyl of white powder bromine behind the suction filtration.
Embodiment 2
Add ethanol 8.87mol, Peng Qinghuana 0.518mol (1.0eq) in three mouthfuls of reaction flasks of 1000ml; After treating that Peng Qinghuana dissolves fully under stirring; At room temperature drip propyl group dicyclohexyl ketone 0.518mol (1.0eq), slowly drip, be allowed to condition at 10 ℃ of reactions after dropwising.The question response system presents more white powder time point plate and confirms to have or not raw material, if do not have, then explanation reacts completely.Resultant of reaction is behind suction filtration, and with the saturated sodium bicarbonate solution washing, and then with clear water washing 3～4 times, through draining, dry the propyl group dicyclohexyl alcohol 0.473mol that obtains water ratio 20%, yield is greater than 92%.Put up mechanical stirring device, add above-mentioned propyl group dicyclohexyl alcohol 0.067mol (1.0eq), again HBr 0.335mol (5eq) is added in the there-necked flask at the there-necked flask of 250ml; Be warming up to 100 ℃ of backflows then; Until the reaction system clear, no white powder raw material takes a plate or survey GC to carry out middle control this moment; See to have or not raw material, till reacting completely.The mode of adopt the separatory extraction, revolving steaming obtains liquid propyl group dicyclohexyl bromine 0.035mol, and content is about 85%, yield about 66.7%.The liquid propyl group dicyclohexyl bromine that obtains is put into freezing in the refrigerator-freezer (temperature is subzero 20 degrees centigrade); Have solid to separate out, suction filtration obtains little yellow solid, and ethanol adds the back temperature rising reflux by 5 times equivalent; After treating that solid dissolves fully; Naturally stir cooling, solid is separated out subsequently, obtains the solid-state propyl group dicyclohexyl of white powder bromine behind the suction filtration.
Embodiment 3
Add methyl alcohol 12.3mol, Peng Qinghuana 0.78mol (1.5eq) in three mouthfuls of reaction flasks of 1000ml; After treating under the agitation condition that Peng Qinghuana dissolves fully; At room temperature drip propyl group dicyclohexyl 0.518mol (1.0eq); Slowly drip, because meeting heat release in the process that drips is allowed to condition at 30 ℃ of insulation reaction after dropwising.The question response system presents more white powder time point plate and confirms to have or not raw material, if do not have, then explanation reacts completely.Resultant of reaction is behind suction filtration, and with the saturated sodium bicarbonate solution washing, and then with clear water washing 3～4 times, through draining, dry the propyl group dicyclohexyl alcohol 0.58mol that obtains water ratio 18%, yield is greater than 91%.Put up mechanical stirring device, add above-mentioned propyl group dicyclohexyl alcohol 0.067mol (1.0eq), again HBr0.536mol (8eq) is added in the there-necked flask at the there-necked flask of 250ml; Be warming up to 120 ℃ of backflows then; Until the reaction system clear, no white powder raw material takes a plate or survey GC to carry out middle control this moment; See to have or not raw material, till reacting completely.The mode that adopts separatory to extract, revolve steaming obtains liquid propyl group dicyclohexyl bromine 0.044mol, content 86.5%, yield about 84%.The liquid propyl group dicyclohexyl bromine that obtains is put into freezing in the refrigerator-freezer (temperature is subzero 20 degrees centigrade); Have solid to separate out, suction filtration obtains little yellow solid, and ethanol adds the back temperature rising reflux by 5 times equivalent; After treating that solid dissolves fully; Naturally stir cooling, solid is separated out subsequently, obtains the solid-state propyl group dicyclohexyl of white powder bromine behind the suction filtration.
Embodiment 4
Add THF (THF) 6.18mol, Peng Qinghuana 1.04mol (2eq) in the four-hole bottle of 1000ml; After treating under the agitation condition that Peng Qinghuana dissolves fully; Drip propyl group dicyclohexyl ketone 0.518mol (1.0eq) at 50 ℃; Rate of addition is wanted suitably to dropwise its room temperature natural reaction of relief.The question response system presents more white powder time point plate and confirms to have or not raw material, if do not have, then explanation reacts completely.Resultant of reaction is behind suction filtration, and with the saturated sodium bicarbonate solution washing, and then with clear water washing 3～4 times, through draining, dry the propyl group dicyclohexyl alcohol 0.45mol that obtains water ratio 17%, yield is greater than 95%.Put up mechanical stirring device, add above-mentioned propyl group dicyclohexyl alcohol 0.067mol (1.0eq), again HBr0.2 (3eq) is added in the there-necked flask at the there-necked flask of 250ml; 110 ℃ are warming up to backflow then; Until the reaction system clear, no white powder raw material takes a plate or survey GC to carry out middle control this moment; See to have or not raw material, till reacting completely.The mode that adopts separatory to extract, revolve steaming obtains liquid propyl group dicyclohexyl bromine 0.03mol, content 82%, yield about 57.4%.The liquid propyl group dicyclohexyl bromine that obtains is put into freezing in the refrigerator-freezer (temperature is subzero 20 degrees centigrade); Have solid to separate out, suction filtration obtains little yellow solid, and ethanol adds the back temperature rising reflux by 5 times equivalent; After treating that solid dissolves fully; Naturally stir cooling, solid is separated out subsequently, obtains the solid-state propyl group dicyclohexyl of white powder bromine behind the suction filtration.
The foregoing description only is a preferred embodiments of the present invention; Technical conceive of the present invention and essential implementation have been specified; Be not to be that protection scope of the present invention is limited; All any simple modification that spirit is done according to the present invention and equivalent structure transformation or modification all should be encompassed within protection scope of the present invention.
Claims (7)
1. the preparation method of propyl group dicyclohexyl bromine is characterized in that, may further comprise the steps:
(1) propyl group dicyclohexyl ketone and Peng Qinghuana generation reduction reaction make propyl group dicyclohexyl alcohol,
Wherein, said solvent is one or more mixtures in water, THF, ethanol or the methyl alcohol,
(2) with the above-mentioned propyl group dicyclohexyl alcohol and Hydrogen bromide generation bromination reaction that makes, resultant of reaction extracts, revolves steaming through separatory and obtains liquid propyl group dicyclohexyl bromine,
(3) the above-mentioned liquid propyl group dicyclohexyl bromine that makes is obtained the solid-state propyl group dicyclohexyl of white powder bromine through freezing, suction filtration, temperature rising reflux, stirring cooling, suction filtration.
2. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: the temperature of reaction of reduction reaction is 0 ℃-110 ℃ in the said step (1), is preferably 10 ℃-60 ℃.
3. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: reduction reaction in the said step (1), the mol ratio of propyl group dicyclohexyl ketone and Peng Qinghuana is 1 ︰ (0.1～5), is preferably 1 ︰ (0.1～2).
4. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: the temperature of reaction of bromination reaction is 90 ℃-150 ℃ in the said step (2), is preferably 100 ℃-120 ℃.
5. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: bromination reaction in the said step (2), propyl group dicyclohexyl alcohol is 1 ︰ (3～20) with hydrobromic mol ratio, is preferably 1 ︰ (3～10).
6. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: said step (1) reduction reaction resultant through suction filtration, wash, drain after as the raw material of step (2) bromination reaction.
7. the preparation method of propyl group dicyclohexyl bromine according to claim 1 is characterized in that: temperature rising reflux reflux state occurs more than being meant and adding ethanol and be warming up to the ethanol boiling point in the said step (3).
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| CN201210032757XA CN102603467A (en) | 2012-02-15 | 2012-02-15 | Preparation method of propyldicyclohexyl bromide |
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| CN201210032757XA CN102603467A (en) | 2012-02-15 | 2012-02-15 | Preparation method of propyldicyclohexyl bromide |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10220549A1 (en) * | 2001-05-25 | 2002-12-05 | Merck Patent Gmbh | New Grignard, organomanganese, organozinc and organic halogen compounds are used in the preparation of decalin, diphenyl, diphenylethane and diphenylethene compounds, used in liquid crystal displays |
| US6716491B2 (en) * | 2000-05-08 | 2004-04-06 | Merck Patent Gmbh | Liquid-crystalline medium |
| CN101704724A (en) * | 2009-11-20 | 2010-05-12 | 烟台德润液晶材料有限公司 | Novel method for preparing high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound |
-
2012
- 2012-02-15 CN CN201210032757XA patent/CN102603467A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716491B2 (en) * | 2000-05-08 | 2004-04-06 | Merck Patent Gmbh | Liquid-crystalline medium |
| DE10220549A1 (en) * | 2001-05-25 | 2002-12-05 | Merck Patent Gmbh | New Grignard, organomanganese, organozinc and organic halogen compounds are used in the preparation of decalin, diphenyl, diphenylethane and diphenylethene compounds, used in liquid crystal displays |
| CN101704724A (en) * | 2009-11-20 | 2010-05-12 | 烟台德润液晶材料有限公司 | Novel method for preparing high-proportion trans, trans-4-(4'-alkyl cyclohexyl) cyclohexyl alcohol liquid crystal intermediate compound |
Non-Patent Citations (2)
| Title |
|---|
| 刘秀杰等: "氢溴酸法制备溴代环戊烷", 《沈阳药科大学学报》, vol. 18, no. 2, 30 March 2001 (2001-03-30), pages 100 - 101 * |
| 樊能廷编著: "《有机合成事典》", 31 May 1995, article "溴代环己烷", pages: 16 * |
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Application publication date: 20120725 |