JP2004010550A - Method for producing deuterated aromatic compound - Google Patents

Abstract

A deuterated aromatic compound having a high deuteration ratio is provided in a simple manner.
An aromatic compound containing at least one benzene ring is reacted with deuterated benzene in the presence of a metal halide containing a transition metal or aluminum from Groups 5 to 6 of the periodic table, and the aromatic compound is reacted with the aromatic compound. The object is achieved by converting hydrogen bonded to a benzene ring in a compound to deuterium at a deuteration ratio of 90% or more.
[Selection diagram] None

Description

【００５５】
表１から明らかなように、金属ハロゲン化物として、五塩化モリブデン、六塩化タングステン、五塩化ニオブ、五塩化タンタル、三塩化アルミニウムを用いた場合には、生成物の重水素化率が９０％以上と極めて高くなることがわかった。また、金属ハロゲン化物として、五塩化モリブデン、五塩化タンタルを用いると、重水素化率が９８％と更に良くなることがわかった。
【００５６】
これに対し、金属ハロゲン化物として、四塩化チタン、四塩化スズを用いた場合は、生成物の重水素化率が極めて悪く、または全く重水素化されないことがわかった。
【００５７】
＜出発物質別の重水素化率および収率の変化＞
出発物質によって重水素化率や収率が異なるかどうかを調べるために、以下の実施例１〜４に示すように、様々な出発物質を用いて重水素化反応を行った。金属ハロゲン化物としては、五塩化モリブデンを使用した。
【００５８】
実施例１
１，１，２−デューテロトリフェニルエタン
五塩化モリブデン（０．１　ｍｍｏｌ）および１０ｍＬのＣ_６Ｄ_６の混合物を、室温にて攪拌し、得られた反応混合物に、１，１，２−トリフェニルエタン　（１　ｍｍｏｌ）を加え、混合物を２４時間攪拌した。３　Ｎ　ＨＣｌを添加して反応を終了させ、有機相をジエチルエーテルで抽出した。抽出物を、水、炭酸水素ナトリウム（２０％水溶液）、水、食塩水の順に洗浄し、次いで、硫酸マグネシウムで乾燥させた。減圧下、溶媒を留去し、粗生成物を得た。得られた残留物をシリカゲルカラムクロマトグラフィーにより精製を行い、表題化合物を得た。標題化合物は、ＮＭＲによって分析を行い、重水素化率を測定した。ＧＣ収率５３％、単離収率４２％、重水素化率９８％。
【００５９】
実施例２
デューテロナフタレン
実施例１と同様の操作を行った。ただし、Ｃ_６Ｄ_６は６ｍＬ使用した。また、攪拌時間を１時間とした。ＧＣ収率８１％、重水素化率９７％。
【００６０】
実施例３
デューテロアントラセン
実施例１と同様の操作を行った。ただし、Ｃ_６Ｄ_６は７ｍＬ使用した。ＧＣ収率７１％、重水素化率９６％。
【００６１】
実施例４
デューテロジフェニルメタン
実施例１と同様の操作を行った。ただし、Ｃ_６Ｄ_６は７ｍＬ使用した。ＧＣ収率７９％、単離収率６５％、重水素化率９６％。
【００６２】
出発物質、反応条件、収率および重水素化率を表２に示す。
【００６３】
【表２】

【００６４】
表２から明らかなように、出発物質にかかわらず、高い重水素化率の重水素化芳香族化合物を得ることができた。
【００６５】
【発明の効果】
本発明の方法によれば、ベンゼン環に結合した水素を極めて高い率で重水素化した重水素化芳香族化合物を得ることができる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to a method for producing a deuterated aromatic compound, and more particularly to a method for converting hydrogen bonded to a benzene ring of an aromatic compound containing one or more benzene rings into deuterium at a high deuteration rate. A method for producing a deuterated aromatic compound.
[0002]
Problems to be solved by the prior art and the invention
Deuterated compounds have a variety of special applications and are in high demand. In addition, a method for providing a deuterated compound having a high deuteration rate has been desired.
[0003]
Therefore, it has been desired to easily obtain a deuterated compound at a high deuteration rate.
[0004]
[Means for Solving the Problems]
That is, in the present invention, an aromatic compound containing at least one benzene ring is reacted with deuterated benzene in the presence of a metal halide containing a transition metal or aluminum from Group 5 to Group 6 of the periodic table, A method for producing a deuterated aromatic compound is provided, wherein hydrogen bonded to a benzene ring in the aromatic compound is converted to deuterium at a deuteration ratio of 90% or more.
[0005]
In the present invention, the deuteration ratio is preferably 97% or more.
[0006]
In the present invention, the metal halide preferably contains molybdenum, niobium, tungsten, tantalum or aluminum, and the metal halide is molybdenum pentachloride, niobium pentachloride, tungsten hexachloride, tantalum pentachloride, or More preferably, it is aluminum trichloride.
[0007]
In the present invention, the aromatic compound is preferably a polycyclic aromatic hydrocarbon, and the polycyclic aromatic hydrocarbon is a ring-assembled aromatic hydrocarbon or a condensed polycyclic aromatic hydrocarbon. Is more preferable.
[0008]
In the present invention, when the aromatic compound is the ring-assembled aromatic hydrocarbon, the ring-assembled aromatic hydrocarbon may be a C _{1 to} C ₂₀ alkane substituted by 2 to 10 aryl groups. And phenylene oligomers such as biphenyl and terphenyl.
[0009]
In the present invention, when the aromatic compound is a condensed polycyclic aromatic hydrocarbon, the condensed polycyclic aromatic hydrocarbon is preferably a 2 to 10-ring condensed aromatic hydrocarbon. , Naphthalene, anthracene, acenaphthylene and phenanthrene are more preferred.
[0010]
BEST MODE FOR CARRYING OUT THE INVENTION
In the present invention, an aromatic compound having at least one benzene ring is reacted with deuterated benzene in the presence of a metal halide, and hydrogen bonded to the benzene ring in the aromatic compound is converted to a deuteration rate of 90%. As described above, there is provided a method for producing a deuterated aromatic compound, characterized in that the compound is converted to deuterium.
[0011]
As used herein, “aromatic compound” refers to a compound containing at least one benzene ring. In the present invention, the aromatic compound may have a substituent introduced therein.
[0012]
In the present specification, when the “aromatic compound” contains two or more benzene rings, two or more benzene rings may be condensed, or two or more benzene rings may be directly connected by a single bond. And may be bonded via an aliphatic hydrocarbon group which may have a substituent. The single bond or the aliphatic hydrocarbon group includes an oxygen atom, a group represented by the formula -C (= O)-, a sulfur atom, a group represented by the formula -C (= S)-, a silicon atom, a tin atom, and a germanium. atom, phosphorus atom or the formula -N (B) - (. wherein, B is a hydrogen atom or a C ₁ -C ₂₀ hydrocarbon group) a group represented by may be interrupted by 1 or more.
[0013]
B is preferably a hydrogen atom or a C _{1 to} C ₁₀ hydrocarbon group, more preferably a hydrogen atom or a C _{1 to} C ₇ hydrocarbon group, and B is a hydrogen atom or a C _{1 to} C ₃ alkyl group. , A phenyl group or a benzyl group.
[0014]
In the present specification, the “hydrocarbon group” may be a saturated or unsaturated acyclic, or may be a saturated or unsaturated cyclic. When the hydrocarbon group is acyclic, it may be linear or branched. The "hydrocarbon _group", C 1 _{-C 20} alkyl _group, C 2 _{-C 20} alkenyl _group, C 2 _{-C 20} alkynyl _group, C 4 _{-C 20} alkadienyl _group, C 6 _{-C 18} aryl group, C ₆ -C ₂₀ alkylaryl _group, C 6 _{-C 20} arylalkyl _group, C 4 _{-C 20} cycloalkyl _group, C 4 _{-C 20} cycloalkenyl _{group, (C} 3 ~C _{10 cycloalkyl)} C 1 _{-C 10} And an alkyl group.
[0015]
In the present specification, _"C 1 _{-C 20} alkyl group" _is preferably C 1 _{-C 10} alkyl _group, more preferably a C 1 -C ₆ alkyl group. Examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, dodecanyl and the like.
[0016]
In the present specification, _"C 2 _{-C 20} alkenyl group" _is preferably C 2 _{-C 10} alkenyl _group, more preferably a C 2 -C ₆ alkenyl group. Examples of the alkenyl group include, but are not limited to, vinyl, allyl, propenyl, isopropenyl, 2-methyl-1-propenyl, 2-methylallyl, 2-butenyl and the like.
[0017]
In the present specification, _"C 2 _{-C 20} alkynyl group" _is preferably C 2 _{-C 10} alkynyl _group, more preferably a C 2 -C ₆ alkynyl group. Examples of alkynyl groups include, but are not limited to, ethynyl, 2-propynyl, 2-butynyl, and the like.
[0018]
In the present specification, _"C 4 _{-C 20} alkyldienyl group" _is preferably C 4 _{-C 10} alkadienyl _group, more preferably a C 4 -C ₆ alkadienyl group. Examples of the alkyldienyl group include, but are not limited to, 1,3-butadienyl and the like.
[0019]
In the present specification, the “C ₆ -C ₁₈ aryl group” is preferably a C ₆ -C ₁₀ aryl group. Examples of the aryl group include, but are not limited to, phenyl, 1-naphthyl, 2-naphthyl, indenyl, biphenylyl, anthryl, phenanthryl and the like.
[0020]
In the present specification, the “C ₆ -C ₂₀ alkylaryl group” is preferably a C ₆ -C ₁₂ alkylaryl group. Examples of alkylaryl groups include, but are not limited to, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 2,4-xylyl, 2,5-xylyl, o-cumenyl, m-tolyl -Cumenyl, p-cumenyl, mesityl and the like.
[0021]
In the present specification, the “C ₆ -C ₂₀ arylalkyl group” is preferably a C ₆ -C ₁₂ arylalkyl group. Examples of arylalkyl groups include, but are not limited to, benzyl, phenethyl, diphenylmethyl, triphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, 2,2-diphenylethyl, 3-phenylpropyl, Examples thereof include phenylbutyl and 5-phenylpentyl.
[0022]
In the present specification, the “C ₄ -C ₂₀ cycloalkyl group” is preferably a C ₄ -C ₁₀ cycloalkyl group. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
[0023]
In the present specification, the “C ₄ -C ₂₀ cycloalkenyl group” is preferably a C ₄ -C ₁₀ cycloalkenyl group. Examples of the cycloalkenyl group include, but are not limited to, cyclopropenyl, cyclobutenyl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl and the like.
[0024]
In the present invention, the number of benzene rings contained in the “aromatic compound” is preferably 2 or more, more preferably 2 to 10.
[0025]
In the present invention, at least one of the benzene rings contained in the “aromatic compound” has at least one hydrogen bonded to the ring.
[0026]
In the present specification, examples of the “aromatic compound” include a monocyclic aromatic hydrocarbon, a polycyclic aromatic hydrocarbon, and the like.
[0027]
Examples of the “monocyclic aromatic hydrocarbon” include unsubstituted benzene and substituted benzene (for example, xylene).
[0028]
Examples of the “polycyclic aromatic hydrocarbon” include a ring-assembled aromatic hydrocarbon and a condensed polycyclic aromatic hydrocarbon.
[0029]
“Ring-assembled aromatic hydrocarbon” refers to a compound in which two or more aromatic hydrocarbons are directly connected by a single bond, or an aliphatic hydrocarbon in which two or more aromatic hydrocarbons may have a substituent. Compounds bonded via a hydrogen group can be given. These aromatic hydrocarbons may have a substituent.
[0030]
Examples of the “aromatic hydrocarbon” included in the “ring-assembled aromatic hydrocarbon” include monocyclic or polycyclic aromatic hydrocarbons, such as benzene, naphthalene, anthracene, acenaphthylene, and phenanthrene. Can be mentioned.
[0031]
Examples of the “compound in which two or more aromatic hydrocarbons are directly connected by a single bond” include a phenylene oligomer having 2 to 20 benzene rings. As the phenylene oligomer, for example, a phenylene oligomer having 2 to 10 benzene rings is preferable, a phenylene oligomer having 2 to 6 benzene rings is more preferable, and biphenyl, triphenyl and the like can be more preferably mentioned.
[0032]
Examples of the “compound in which two or more aromatic hydrocarbons are bonded via an aliphatic hydrocarbon group” include C ₁ -C ₂₀ alkanes substituted by 2-10 aryl groups.
[0033]
Examples of the “aryl group” of the “C ₁ -C ₂₀ alkane substituted by 2-10 aryl groups” include C ₆ -C ₁₀ aryl groups, for example, phenyl, 1-naphthyl, 2-naphthyl , Indenyl, biphenylyl, anthryl and phenanthryl.
[0034]
_"C 1 _{-C 20} alkane" in _"C 1 _{-C 20} alkane substituted by 2 to 10 aryl group" _is preferably C 1 _{-C 10 alkane,} it is C 1 -C ₆ alkane Is more preferred. Examples of C ₁ -C ₂₀ alkanes, but are not limited to, it may be mentioned methane, ethane, propane, butane, pentane, hexane and the like.
[0035]
The “C ₁ -C ₂₀ alkane substituted with 2 to 10 aryl groups” is preferably a C _{1 to} C ₂₀ alkane substituted with 2 to 6 aryl groups, and is preferably a C _{1 to} C ₂₀ alkane substituted with 2 to 6 aryl groups. more preferably substituted _C 1 _{-C 10} alkanes. For example, 1,1,2-triphenylethane, diphenylmethane and the like can be mentioned.
[0036]
Examples of the “condensed polycyclic aromatic hydrocarbon” include a compound in which two or more aromatic hydrocarbons are condensed, and a 2 to 10-ring condensed aromatic hydrocarbon is preferable, and a 2 to 6 ring It is more preferably a formula-condensed aromatic hydrocarbon, and even more preferably a 2- to 4-cyclic condensed aromatic hydrocarbon. These aromatic hydrocarbons may have a substituent.
[0037]
Examples of "fused polycyclic aromatic hydrocarbons" include, but are not limited to, naphthalene, anthracene, acenaphthylene, and phenanthrene.
[0038]
In the present specification, "aromatic compounds", "aliphatic hydrocarbon group", "benzene" listed as "monocyclic aromatic hydrocarbon", "ring-containing aromatic hydrocarbon" contains "aromatic" A substituent may be introduced into the "aromatic hydrocarbon" contained in the "hydrocarbon" and the "condensed polycyclic aromatic hydrocarbon". Examples of the substituent include a C ₁ -C ₁₀ hydrocarbon group (eg, methyl, ethyl, propyl, butyl, etc.), a C ₁ -C ₁₀ alkoxy group (eg, methoxy, ethoxy, propoxy, butoxy, etc.), ₁ -C ₁₀ alkylthio group (e.g., methylthio, ethylthio, propylthio, _butylthio), C 6 _{-C 10} aryloxy group (e.g., phenyloxy, naphthyloxy, biphenyloxy, _etc.), C 6 _{-C 10} arylthio group (e.g., phenylthio, naphthylthio, biphenyl thio, _etc.), C 1 _{-C 10} alkoxy - carbonyl group (e.g., methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, _{t-butoxycarbonyl),} C 6 _{-C 10} aryloxy - carbonyl group (e.g., methoxy Carbonyl, ethoxy Carbonyl, propoxycarbonyl, _{t-butoxycarbonyl),} C 1 _{-C 10} alkyl - carbonyl group (e.g., acetoxy, _{propanoyloxy),} C 6 _{-C 10} aryl - carbonyl group (e.g., benzoyloxy, 1-naphtho Yloxy, 2-naphthoyloxy), a carbamoyl group which may have a substituent, an amino group which may have a substituent, a nitro group, a cyano group, a hydroxyl group, and a halogen atom (for example, fluorine, chlorine , Bromine, iodine), a group containing phosphorus (eg, alkylphosphino, dialkylphosphino), a group containing germanium, a group containing tin, a group containing silicon, and the like. In this case, one or more substituents may be introduced at substitutable positions, and preferably one to four substituents may be introduced. When the number of substituents is two or more, each substituent may be the same or different.
[0039]
Examples of the “substituent” that each of the “carbamoyl group optionally having a substituent” and “amino group optionally having a substituent” may have, for example, C ₁ to C _{1 10} hydrocarbon groups (eg, methyl, ethyl, propyl, butyl, etc.), C ₁ -C ₁₀ alkoxy groups (eg, methoxy, ethoxy, propoxy, butoxy, etc.), hydroxyl groups, halogen atoms (eg, fluorine, chlorine, bromine, Iodine) and the like.
[0040]
In the method for producing a deuterated aromatic compound according to the present invention, the reaction is performed in the presence of a metal halide.
[0041]
In the present invention, the metal halide contains a transition metal of Groups 5 to 6 of the periodic table or aluminum, and preferably contains molybdenum, niobium, tungsten, tantalum or aluminum.
[0042]
In the present invention, examples of the metal halide include molybdenum (V) halide, niobium (V) halide, tungsten (VI) halide, tantalum (V) halide, and aluminum (III) halide. Preferably, molybdenum pentachloride, niobium pentachloride, tungsten hexachloride, tantalum pentachloride, or aluminum trichloride can be preferably exemplified.
[0043]
In the present invention, the amount of the metal halide is appropriately determined in consideration of the number of hydrogen bonded to the benzene ring of the aromatic compound to be reacted, but is generally 0.0001 to 1 mol of the aromatic compound. It is preferably from 5 mol to 5 mol, more preferably from 0.001 mol to 1 mol, and still more preferably from 0.01 mol to 1 mol.
[0044]
In the method for producing a deuterated aromatic compound of the present invention, the aromatic compound is reacted with deuterated benzene in the presence of a metal halide.
[0045]
In the present invention, when deuterating hydrogen on the benzene ring in an aromatic compound using deuterated benzene, the presence of a predetermined metal halide surprisingly results in a hydrogen-deuterium exchange reaction. Was found to proceed in an equilibrium reaction. Therefore, by reacting an excess amount of deuterated benzene with respect to the amount of the aromatic compound, the hydrogen-deuterium exchange reaction is tilted in the direction of deuteration, and the aromatic compound has a very high deuteration rate. Deuteration could be realized.
[0046]
In the present invention, the amount of deuterated benzene is preferably used in an amount of 1 mol or more per 1 mol of the aromatic compound, and more preferably an excess amount. In particular, it is preferable to use deuterated benzene as the solvent.
[0047]
The reaction is appropriately determined according to the type of the compound to be reacted and the metal halide, and is preferably performed, for example, in a temperature range of −10 ° C. to 300 ° C., and particularly preferably in a temperature range of −0 ° C. to 200 ° C. More preferably, it is carried out in a temperature range of 0 ° C to 60 ° C. The pressure is, for example, in the range from 0.1 bar to 2500 bar, preferably in the range from 0.5 bar to 10 bar.
[0048]
As the solvent, a solvent that can dissolve the aromatic compound is preferable. As the solvent, an aliphatic or aromatic organic solvent is used. Ether solvents such as tetrahydrofuran or diethyl ether; halogenated hydrocarbons such as methylene chloride; halogenated aromatic hydrocarbons such as o-dichlorobenzene; amides such as N, N-dimethylformamide; sulfoxides such as dimethylsulfoxide; Aromatic hydrocarbons such as benzene, toluene and deuterated benzene are used. It is particularly preferred to use deuterated benzene.
[0049]
According to the present invention, a deuterated aromatic compound having a deuteration ratio of 90% or more can be obtained, and the deuteration ratio can be easily increased by increasing the amount of deuterated benzene relative to the aromatic compound. For example, a deuteration ratio of 97% or more, or 99% or more can be realized.
[0050]
【Example】
Hereinafter, the present invention will be described based on examples. However, the present invention is not limited to the following examples.
[0051]
All reactions were performed under a dry nitrogen atmosphere unless otherwise noted. Reagents were purchased from commercial sources and used as they were.
[0052]
<Change in deuteration rate for each metal halide>
In order to investigate how the metal halide affects the deuteration rate, a deuteration reaction of an aromatic compound was performed using various metal halides. Naphthalene was used as starting material. As the metal halide, molybdenum pentachloride, tungsten hexachloride, niobium pentachloride, tantalum pentachloride, aluminum trichloride, titanium tetrachloride, and tin tetrachloride were used.
[0053]
The reaction was performed as follows. That is, a mixture of the metal halide (0.1 mmol) shown in Table 1 and 6 mL of C ₆ D ₆ was stirred at room temperature, and naphthalene (1 mmol) was added to the obtained reaction mixture. Further, the mixture was stirred for the reaction time shown in Table 1. The reaction was quenched by adding 3 N HCl and the organic phase was extracted with diethyl ether. The extract was washed with water, sodium bicarbonate (20% aqueous solution), water and brine in that order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The obtained residue was purified by silica gel column chromatography to give the title compound. The title compound was analyzed by NMR, and the deuteration ratio was measured. Table 1 shows the obtained deuteration ratios. In the table, M in “MCl ₅ to ₆ ” indicates a metal.
[0054]
[Table 1]

[0055]
As is clear from Table 1, when molybdenum pentachloride, tungsten hexachloride, niobium pentachloride, tantalum pentachloride, or aluminum trichloride is used as the metal halide, the deuteration ratio of the product is 90% or more. It turned out to be extremely high. It was also found that the use of molybdenum pentachloride or tantalum pentachloride as the metal halide further improved the deuteration ratio to 98%.
[0056]
On the other hand, when titanium tetrachloride or tin tetrachloride was used as the metal halide, it was found that the deuteration rate of the product was extremely poor, or the product was not deuterated at all.
[0057]
<Changes in deuteration rate and yield by starting material>
In order to determine whether the deuteration rate and yield differ depending on the starting materials, deuteration reactions were performed using various starting materials as shown in Examples 1 to 4 below. Molybdenum pentachloride was used as the metal halide.
[0058]
Example 1
A mixture of 1,1,2-deuterotriphenylethane molybdenum pentachloride (0.1 mmol) and 10 mL of C ₆ D ₆ was stirred at room temperature, and the resulting reaction mixture was added to 1,1,2- Triphenylethane (1 mmol) was added and the mixture was stirred for 24 hours. The reaction was quenched by adding 3 N HCl and the organic phase was extracted with diethyl ether. The extract was washed with water, sodium bicarbonate (20% aqueous solution), water and brine in that order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product. The obtained residue was purified by silica gel column chromatography to give the title compound. The title compound was analyzed by NMR, and the deuteration ratio was measured. GC yield 53%, isolation yield 42%, deuteration rate 98%.
[0059]
Example 2
Deuteronaphthalene The same operation as in Example 1 was performed. However, ₆ mL of C ₆ D ₆ was used. The stirring time was 1 hour. GC yield 81%, deuteration rate 97%.
[0060]
Example 3
The same operation as in Deuteroanthracene Example 1 was performed. However, 7 mL of C ₆ D ₆ was used. GC yield 71%, deuteration rate 96%.
[0061]
Example 4
Deuterodiphenylmethane The same operation as in Example 1 was performed. However, 7 mL of C ₆ D ₆ was used. GC yield 79%, isolation yield 65%, deuteration rate 96%.
[0062]
The starting materials, reaction conditions, yields and deuteration rates are shown in Table 2.
[0063]
[Table 2]

[0064]
As is evident from Table 2, regardless of the starting material, a deuterated aromatic compound having a high deuteration ratio could be obtained.
[0065]
【The invention's effect】
According to the method of the present invention, a deuterated aromatic compound in which hydrogen bonded to a benzene ring is deuterated at an extremely high rate can be obtained.

Claims (11)

Reacting an aromatic compound containing at least one benzene ring with deuterated benzene in the presence of a metal halide containing a transition metal or aluminum from Groups 5 to 6 of the periodic table, and reacting benzene in the aromatic compound with A method for producing a deuterated aromatic compound, comprising converting hydrogen bonded to a ring to deuterium at a deuteration rate of 90% or more. The method for producing a deuterated aromatic compound according to claim 1, wherein the deuteration ratio is 97% or more. The method for producing a deuterated aromatic compound according to claim 2, wherein the metal halide contains molybdenum, niobium, tungsten, tantalum, or aluminum. The method for producing a deuterated aromatic compound according to claim 3, wherein the metal halide is molybdenum pentachloride, niobium pentachloride, tungsten hexachloride, tantalum pentachloride, or aluminum trichloride. The method for producing a deuterated aromatic compound according to any one of claims 1 to 4, wherein the aromatic compound is a polycyclic aromatic hydrocarbon. The method for producing a deuterated aromatic compound according to claim 5, wherein the polycyclic aromatic hydrocarbon is a ring-assembled aromatic hydrocarbon. Method of manufacturing a ring assembly aromatic hydrocarbons, deuterated aromatic compound according to claim 6, characterized in that the C ₁ -C ₂₀ alkanes substituted by an aryl group having 2 to 10. The method for producing a deuterated aromatic compound according to claim 6, wherein the ring-assembled aromatic hydrocarbon is a phenylene oligomer. The method for producing a deuterated aromatic compound according to claim 5, wherein the polycyclic aromatic hydrocarbon is a condensed polycyclic aromatic hydrocarbon. The method for producing a deuterated aromatic compound according to claim 9, wherein the condensed polycyclic aromatic hydrocarbon is a condensed 2- to 10-cyclic aromatic hydrocarbon. The method for producing a deuterated aromatic compound according to claim 10, wherein the fused polycyclic aromatic hydrocarbon is naphthalene, anthracene, acenaphthylene, or phenanthrene.