JP2000302720A - Production of biphenyl derivative - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce the subject compound in high yield by adding and reacting a nickel salt, a tertiary phosphine or a tertiary phosphite with an arylboronic acid and an aromatic compound in the presence of a base and an aromatic hydrocarbon solvent in the coexistence of an alcohol. SOLUTION: A nickel salt and a tertiary phosphine or a tertiary phosphite are added and reacted with (A) an arylboronic acid, its derivative or an arylboronic anhydride represented by formula I or II (R is H, a 1-6C alkyl or the like; Y is OH, a group represented by formula III or the like) (e.g. phenylboronic acid or p-aminophenylboronic acid) is reacted with (B) an aromatic compound represented by the formula A-D-X (A is H, a 1-6C alkyl or the like; D is phenylene, naphthylene, furandiyl or the like; and X is Cl, Br, I, mesylate or the like) (e.g. chlorobenzene) in the presence of a base and an aromatic hydrocarbon solvent in the coexistence of an alcohol to thereby produce a biphenyl derivative represented by formula IV. The component A is preferably used on an amount of 0.8-1.5 mol based on 1 mol of the component B.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a biphenyl derivative useful as a liquid crystal raw material and an intermediate for medical and agricultural chemicals.

[0002]

2. Description of the Related Art Conventionally, as a method for synthesizing a biaryl derivative using a boron compound, a method using a palladium or nickel complex as a catalyst is known. However, it is economically and industrially necessary to use a less expensive nickel complex catalyst. Preferred from a standpoint. Examples of the production method using a nickel complex catalyst include (A) a method in which an arylboronic acid and an aryl chloride are allowed to act in the presence of a divalent nickel complex and tripotassium phosphate anhydride (AF Indolese, Tetrahedron Lett)
ers, 38, 3513-3516 (1997)), (B) A method of reacting an aryl boronic acid with an aryl mesylate or an aryl arene sulfonate in the presence of a divalent nickel complex, zinc and tripotassium phosphate anhydrous (V. Percecet al, J. Or
g. Chem., 60, 1060-1065 (1995)), (C) A method in which an arylboronic acid and an aromatic chloride are allowed to act in the presence of a zero-valent nickel complex, a base, and an aprotic polar solvent (S. Sa)
ito et al, Tetrahedron Letters, 37, 2993-2996 (199
6), S. Saito et al, J. Org. Chem., 62,8024-8030 (199
7))), (D) A method of reacting an arylboronic acid or an arylboronic acid ester with an aryl halide or an arylfluoroalkylsulfonate in the presence of a zero-valent or divalent nickel complex, a base, and an aprotic polar solvent JP-A-2-131436, JP-A-Hei 3-2
No. 71243) is known.

However, in each of the above methods (A), (B), (C) and (D), a nickel phosphine complex is used as a catalyst, and a complex catalyst is prepared in advance prior to the reaction. The industrial production method has the disadvantage that the steps are complicated, such as the necessity of separation. Even if a mixture of nickel salt and tertiary phosphine is simply used as a catalyst for the purpose of shortening the process, a nickel phosphine complex having sufficient catalytic activity is not efficiently produced in the reaction system, and the target compound is produced only in a low yield. Cannot be obtained. Moreover, (A),
The methods (B), (C) and (D) are disadvantageous in terms of the production method due to the variation in yield, poor reproducibility, and low production efficiency due to low reaction rate (long reaction time). Had become a major problem.

[0004]

An object of the present invention is to prepare a sufficiently active nickel phosphine complex catalyst directly in a reaction system without isolation, and to prepare an arylboronic acid, a derivative thereof or an arylboronic anhydride from an arylboronic acid. It is an object of the present invention to provide an economical, convenient, and industrially useful method for obtaining a biphenyl derivative in a short time with high yield and good reproducibility.

[0005]

Means for Solving the Problems As a result of intensive studies on the above-mentioned problems, the present inventors have found that arylboronic acid, its derivative or arylboronic anhydride and an aromatic compound can be converted into a base and an aromatic hydrocarbon solvent. When reacting in the presence of a nickel salt and a tertiary phosphine or phosphite in the presence of an alcohol, a nickel phosphine complex having a high catalytic activity is efficiently formed in the reaction system, and the target reaction proceeds smoothly. It has been surprisingly found that a biphenyl derivative can be obtained in a high yield in a short time by the effect of the addition of alcohol, and the present invention has been achieved.

That is, the present invention provides a compound represented by the following general formula (I) or (II):

Embedded image (R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally having up to 6 alkyl groups, 2 carbon atoms
Alkenyl group having 6 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, cyano group, formyl group, acyl group having 2 to 7 carbon atoms, carbon number A benzoyl group optionally having 1 to 6 alkyl groups, an alkoxycarbonyl group having 2 to 7 carbon atoms, a phenoxycarbonyl group optionally having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms Having an amino group which may have a group, an amide group which may have an alkyl group having 1 to 6 carbon atoms, a nitro group, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms. A sulfonyl group having a phenyl group, an alkyl group having 1 to 6 carbon atoms or a sulfonic acid ester group having a phenyl group which may have an alkyl group having 1 to 6 carbon atoms, fluorine, or 1 to 6 carbon atoms Of the fluoroalkyl group And, Y is a hydroxyl group, a carbon number 1 to 6
An phenoxy group, a cyclohexyloxy group which may have an alkyl group having 1 to 6 carbon atoms,

Embedded image (In each formula, q is 1, 2, 3 or 4, and r and s are each 2, 3, 4 or 5). ), A derivative thereof or an arylboronic anhydride represented by the following general formula (II)
I)

Embedded image (A is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally having up to 6 alkyl groups, 2 carbon atoms
Alkenyl group having 6 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, cyano group, formyl group, acyl group having 2 to 7 carbon atoms, carbon number A benzoyl group optionally having 1 to 6 alkyl groups, an alkoxycarbonyl group having 2 to 7 carbon atoms, a phenoxycarbonyl group optionally having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms Having an amino group which may have a group, an amide group which may have an alkyl group having 1 to 6 carbon atoms, a nitro group, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms. A sulfonyl group having an optionally substituted phenyl group, an alkyl group having 1 to 6 carbon atoms or a sulfonate group having a phenyl group optionally having an alkyl group having 1 to 6 carbon atoms, fluorine or an alkyl group having 1 to 6 carbon atoms Shows a fluoroalkyl group , D is shown phenylene, naphthylene, pyridine-diyl, quinolinediyl, pyrimidinediyl, triazinediyl, furandiyl, benzo furandiyl, shows a thiophenediyl or benzothiophene diyl, X is chlorine, bromine, iodine, a mesylate group, and arenesulfonate group. When the aromatic compound represented by the formula (1) is reacted in the presence of a base and an aromatic hydrocarbon solvent, a tertiary phosphine or a tertiary phosphite, a nickel salt and an alcohol are added. IV)

Embedded image (R, A, and D are the same as described above.)

[0007]

Embodiments of the present invention will be described below in more detail.

An arylboronic acid represented by the above general formula (I) or (II) used in the method of the present invention;
Examples of the derivatives or arylboronic anhydrides include phenylboronic acid; alkyl-substituted phenylboronic acids such as p-methylphenylboronic acid and m-isopropylphenylboronic acid; and alkenyl-substituted phenylboronic acids such as p-isopropenylphenylboronic acid. Alkynyl-substituted phenylboronic acids such as p-ethynylphenylboronic acid;
aryl-substituted boronic acids such as p-biphenylboronic acid;
alkoxy-substituted phenylboronic acids such as m-methoxyphenylboronic acid and p-butoxyphenylboronic acid;
Alkylthio-substituted phenylboronic acids such as methylthiophenylboronic acid; cyano-substituted phenylboric acids; formyl-substituted phenylboric acids; acyl-substituted phenylboric acids such as p-acetylphenylboric acid; aroyl-substituted phenylboric acids such as p-benzoylphenylboric acid; Alkoxycarbonyl-substituted phenylboric acids such as methoxycarbonylphenylboric acid; phenoxycarbonyl-substituted phenylboric acids such as p-methylphenoxycarbonylphenylboric acid; amino-substituted phenylboric acids such as p-aminophenylboric acid and p-dimethylaminophenylboric acid; Amide-substituted phenylboric acids such as p-carbamoylphenylboric acid and p-monomethylcarbamoylphenylboric acid; p-methylsulfonylphenylboric acid, p-
Sulfonyl-substituted phenylboric acids such as tolylsulfonylphenylboric acid; fluorophenylboric acids; fluoroalkyl-substituted phenylboric acids such as trifluoromethylphenylboric acid; esters thereof such as alkyl esters and phenyl esters; and acid anhydrides thereof. Can be mentioned. These arylboronic acids or derivatives thereof may be used in combination of two or more.

The aromatic compound represented by the above general formula (III), which is another raw material used in the method of the present invention, includes, for example, when D is a phenylene group, halogen compounds such as chlorobenzene and p-bromotoluene. Benzenes;
halogenated benzenes such as p-chlorobenzaldehyde; halogenated anisoles such as m-chloroanisole and p-chloro (2-methoxymethyl) benzene; halogenated benzonitrile such as o-chlorobenzonitrile and p-chlorobenzonitrile Halogenated benzoic acid esters such as methyl o-chlorobenzoate and methyl p-bromobenzoate; p-chloroaniline, p-chloro-N, N-
Halogenated anilines such as dimethylaniline; Halogenated benzoamides such as p-iodobenzoamide, p-chloro-N, N-dimethylbenzoamide; Halogenation such as p-chloroacetophenone and p-bromobenzophenone Examples include acylbenzenes and halogenated benzenes having a plurality of substituents such as 2,4-dimethoxy-5-aminochlorobenzene.

In the general formula (III), D represents phenylene, naphthylene, pyridinediyl, pyrimidinediyl,
It represents a triazinediyl, quinolinediyl, furandiyl, benzofurandiyl, thiophendiyl or benzothiophendiyl group, and the structural formula of the corresponding aromatic compound is represented by the following general formulas (III-1) to (III-1).
It is represented by (III-13). Preferred X is chlorine, bromine, iodine or the like, and preferred A is hydrogen, an alkyl group, an acyl group, an aroyl group, an alkoxy group, a cyano group, an aldehyde group, a carboxylic acid ester group, an amide group or an amino group. Is as shown in the above examples.

[0011]

Embedded image

The ratio of the arylboronic acid represented by the general formula (I) or the derivative thereof to the aromatic compound represented by the general formula (III) is determined from the viewpoint of economy and reactivity.
Usually, the arylboronic acid or its derivative is used in an amount of 0.8 to 1 mol per mol of the aromatic compound represented by the general formula (III).
The amount is 1.5 mol, preferably 1 to 1.3 mol. Also,
Similarly, the ratio of the arylboronic anhydride represented by the general formula (II) to the aromatic compound represented by the general formula (III) is the same as that of the aromatic compound represented by the general formula (III). Arylboronic anhydride 0.3 to 1 mol
It is 0.5 mol, preferably 0.33 to 0.43 mol.

The aromatic hydrocarbon solvent used in the present invention includes, for example, benzene, toluene, xylene, mesitylene, ethylbenzene, n-propylbenzene and i-propylbenzene.
and so-propylbenzene. Although the amount of use is not particularly limited, it is usually 700 to 100 parts by weight of the aromatic compound represented by the general formula (III).
About 3000 parts by weight is industrially preferable from the viewpoint of operability and economy.

The nickel salt used as the catalyst of the present invention includes, for example, nickel chloride hexahydrate, anhydrous nickel chloride, nickel bromide trihydrate, anhydrous nickel bromide, nickel iodide hexahydrate, anhydrous iodine Nickel halides such as nickel halide, nickel nitrate hexahydrate, nickel nitrates such as anhydrous nickel nitrate, nickel sulfate heptahydrate, nickel sulfate such as anhydrous nickel sulfate and nickel sulfate, nickel acetate tetrahydrate , Anhydrous nickel acetate, nickel oxalate dihydrate,
Nickel organic carboxylate such as anhydrous nickel oxalate, nickel acetylacetonate dihydrate, nickel acetylacetonate complex salts such as anhydrous nickel acetylacetonate,
Nickel hydroxide and the like. From the viewpoints of economy and reactivity, the amount of use is 0.005 to 0.1 mol per 1 mol of the aromatic compound represented by the general formula (III),
Preferably it is 0.01 to 0.03 mol.

The tertiary phosphine or tertiary phosphite used in the present invention is, for example, triphenylphosphine, tolylphosphine, methyldiphenylphosphine, dimethylphenylphosphine, trimethylphosphine, triethylphosphine, tributylphosphine, tricyclohexylphosphine, , 2-bisdiphenylphosphinoethane, 1,3-bisdiphenylphosphinopropane, 1,4-bisdiphenylphosphinobutane,
Examples thereof include 1,1′-bisdiphenylphosphinoferrocene, triphenyl phosphite, tolyl phosphite, trimethyl phosphite, triethyl phosphite, tributyl phosphite, and tricyclohexyl phosphite. The amount of use is 1 to 6 mol, preferably 2 to 4 mol, per 1 mol of the nickel salt from the viewpoint of economy and reactivity.

The alcohols used in the present invention include, for example, methanol, ethanol, n-propanol, is
o-propanol, n-butanol, iso-butanol, sec-butanol, tert-butanol and the like. The amount used is determined according to the formula (III)
Is preferably 0.5 to 10 mol per 1 mol of the aromatic compound represented by the formula: If the alcohol is not added or the amount is less than the above-mentioned predetermined amount, the yield is low and the reaction rate is low.On the other hand, if the amount is too large, the catalyst is deactivated, and satisfactory reaction results and reaction rates cannot be obtained. .

The base used in the present invention includes a hydroxide of an alkali metal or a salt thereof with a weak acid, a hydroxide of an alkaline earth metal or a salt thereof with a weak acid, and a hydroxide of a quaternary ammonium or a weak acid thereof. And the like. Preferred are sodium hydroxide, potassium hydroxide, sodium carbonate, cesium carbonate, tripotassium phosphate and tripotassium phosphate dihydrate. The amount used is 1 to 1 mole of the aromatic compound represented by the general formula (II).
５5 mol, preferably 1-3 mol.

The most important thing in the method of the present invention is that the aryl boric acid represented by the general formula (I) or (II) or a derivative thereof and the aromatic compound represented by the general formula (III) are converted into a base. And tertiary phosphine or a tertiary phosphite, a nickel salt and an alcohol during the reaction in the presence of an aromatic hydrocarbon solvent.
Due to the presence of an appropriate amount of alcohol, the tertiary phosphine or tertiary phosphite and the nickel salt smoothly form a highly active nickel complex catalyst in the reaction system to promote the target reaction. It is also extremely effective in improving the yield, and the synergistic effect of these makes it possible to industrially very simply and efficiently produce the desired biphenyl derivative.

In the method of the present invention, it is important to react after adding tertiary phosphine or tertiary phosphite, a nickel salt and an alcohol to the reaction system, and the addition method, the order of addition and the like are not particularly limited. For example, a method of adding an alcohol solution of a tertiary phosphine or a tertiary phosphite and a nickel salt to an aromatic hydrocarbon solvent, and then charging and reacting an arylboronic acid or a derivative thereof, an aromatic compound and a base, an aromatic hydrocarbon solvent Various charging methods are possible, such as a method in which arylboronic acid or a derivative thereof, an aromatic compound, a base, tertiary phosphine or tertiary phosphite, a nickel salt and an alcohol are added in random order, followed by a reaction. Also preferably used is a two-step reaction method in which a tertiary phosphine or tertiary phosphite, a nickel salt and an alcohol are used to form a nickel complex in a hydrocarbon, and then an arylboronic acid and an aromatic compound are subjected to a coupling reaction in the presence of a base. Can be

In the method of the present invention, the reaction temperature is from 50 to 12
0 ° C, preferably 60 to 100 ° C. The reaction time varies depending on the reaction temperature, the amount of the catalyst and the like, but is usually 1 to 15 hours, preferably 2 to 10 hours. When the reaction is carried out separately in the nickel complex preparation step and the coupling reaction step, the former is performed at a reaction temperature of 50 to 80 ° C. and a reaction time of 5 to
The reaction temperature may be about 60 to 120 ° C. and the reaction time may be about 2 to 10 hours. The reaction is preferably performed in an inert gas atmosphere to prevent the catalyst from being deactivated by oxygen during the reaction. For example, a nitrogen gas, an argon gas, or the like is used. Although the reaction pressure is not particularly limited, it is usually carried out at atmospheric pressure.

Thus, the biphenyl derivative represented by the general formula (III), which is the target compound of the present invention, is obtained, but a purification operation may be performed to improve the purity of the biphenyl derivative. For example, after adding hydrochloric acid to the reaction solution and separating it into two layers, the layers are separated, washed with an aqueous sodium hydroxide solution, an aqueous sodium hypochlorite solution, a saturated saline solution, and the like, and then concentrated, crystallized, and crystallized. To obtain a highly purified product. The treatment may be performed with silica gel, alumina, or the like.

[0022]

EXAMPLES Hereinafter, the effects of the present invention will be described more specifically based on examples, but the present invention is not limited to the following examples.

EXAMPLE 1 0.47 of triphenylphosphine was placed in a 300 ml reactor.
g (1.8 mmol) and 110 ml of toluene.
The temperature was raised to 70 ° C. To the solution, 0.21 g (0.90 mmol) of nickel chloride hexahydrate dissolved in 1.8 ml (30.6 mmol) of ethanol was added to obtain a yellow slurry. Next, after cooling to room temperature, 5.31 g (39.0 mmol) of p-methylphenylboronic acid, 4.20 g (30.0 mmol) of p-chlorobenzaldehyde, and 15 g of tripotassium phosphate n-hydrate (65. 2 mmol) and stirred at room temperature for 30 minutes. 80 ℃
Then, the reaction was continued for 7 hours. After completion of the reaction, the mixture was cooled to room temperature, and 100 ml of water was added to stop the reaction. 20 ml of 2% hydrochloric acid was added thereto, and liquid separation was performed. When the obtained organic layer was analyzed by gas chromatography, the yield of 4-formyl-4′-methyl-1,1′-biphenyl was 90% based on p-chlorobenzaldehyde.
Met.

Example 2 The same operation as in Example 1 was repeated except that ethanol was replaced with methanol as the alcohol. The yield of 4-formyl-4'-methyl-1,1'-biphenyl is p-
It was 83% based on chlorobenzaldehyde.

Example 3 A reaction between phenylboronic acid and p-chlorobenzonitrile was carried out in the same manner as in Example 1. The yield of 4-cyano-1,1'-biphenyl is 92% based on p-chlorobenzonitrile.
Met.

Example 4 A reaction between p-methylphenylboronic acid and 4-chloroanisole was carried out in the same manner as in Example 1. 3-methoxy-4'-
The yield of methyl-1,1′-biphenyl was 87% based on 4-chloroanisole.

Comparative Example 1 The same operation as in Example 1 was repeated except that the nickel salt was not dissolved in the alcohol but was added as it was. The yield of 4-formyl-4′-methyl-1,1′-biphenyl was 62% based on p-chlorobenzaldehyde.

Comparative Example 2 The same operation as in Example 1 was repeated except that the nickel salt was not dissolved in alcohols but was dissolved in water. The yield of 4-formyl-4′-methyl-1,1′-biphenyl was 27% based on p-chlorobenzaldehyde.

Example 5 A reaction between p-methylphenylboronic acid and 3-chloropyridine was carried out in the same manner as in Example 1. The yield of p-tolyl-3-pyridine was 71% based on 3-chloropyridine.

[0030]

According to the production method of the present invention, a so-called one-pot reaction is carried out directly using a nickel salt, which is an inexpensive catalyst material, and tertiary phosphine or tertiary phosphite and alcohol without isolating and purifying the complex catalyst. The biphenyl derivative can be produced economically, conveniently and industrially in a high yield. The coexistence of alcohols acts very effectively not only in the step of forming a highly active nickel complex catalyst but also in the subsequent coupling reaction step. These synergistic effects not only shorten the production step but also improve the yield, It dramatically improves the reaction results, such as shortening the reaction time by improving the reaction rate and preventing variation in the reaction yield by improving the reproducibility of the reaction.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI theme coat ゛ (Reference) C07C 253/30 C07C 253/30 255/50 255/50 C07D 213/127 C07D 213/127 213/16 213 / 16 // C07B 61/00 300 C07B 61/00 300 F term (reference) 4C055 AA01 BA01 CA08 DA01 FA03 FA31 FA34 FA37 4H006 AA02 AC24 BA02 BA06 BA21 BA29 BA32 BA50 BA53 BB11 BB14 GP03 QN30 4H039 CA41 CD20 CD90

Claims (1)

[Claims] 1. A compound represented by the following general formula (I) or (II): (R is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally having up to 6 alkyl groups, 2 carbon atoms
Alkenyl group having 6 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, cyano group, formyl group, acyl group having 2 to 7 carbon atoms, carbon number A benzoyl group optionally having 1 to 6 alkyl groups, an alkoxycarbonyl group having 2 to 7 carbon atoms, a phenoxycarbonyl group optionally having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms Having an amino group which may have a group, an amide group which may have an alkyl group having 1 to 6 carbon atoms, a nitro group, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms. A sulfonyl group having a phenyl group, an alkyl group having 1 to 6 carbon atoms or a sulfonic acid ester group having a phenyl group which may have an alkyl group having 1 to 6 carbon atoms, fluorine, or 1 to 6 carbon atoms Of the fluoroalkyl group And, Y is a hydroxyl group, a carbon number 1 to 6
An alkoxy group, a phenoxy group optionally having an alkyl group having 1 to 6 carbon atoms, a cyclohexyloxy group, or a compound represented by the following general formula a, b, or c: (In each formula, q is 1, 2, 3 or 4, and r and s are each 2, 3, 4 or 5). ), A derivative thereof or an arylboronic anhydride represented by the following general formula (II)
I) (A is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, 1 carbon atom
A phenyl group optionally having up to 6 alkyl groups, 2 carbon atoms
Alkenyl group having 6 to 6 carbon atoms, alkynyl group having 2 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, alkylthio group having 1 to 6 carbon atoms, cyano group, formyl group, acyl group having 2 to 7 carbon atoms, carbon number A benzoyl group optionally having 1 to 6 alkyl groups, an alkoxycarbonyl group having 2 to 7 carbon atoms, a phenoxycarbonyl group optionally having 1 to 6 carbon atoms, and an alkyl having 1 to 6 carbon atoms Having an amino group which may have a group, an amide group which may have an alkyl group having 1 to 6 carbon atoms, a nitro group, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms. A sulfonyl group having an optionally substituted phenyl group, an alkyl group having 1 to 6 carbon atoms or a sulfonate group having a phenyl group optionally having an alkyl group having 1 to 6 carbon atoms, fluorine or an alkyl group having 1 to 6 carbon atoms Shows a fluoroalkyl group , D is shown phenylene, naphthylene, pyridine-diyl, quinolinediyl, pyrimidinediyl, triazinediyl, furandiyl, benzo furandiyl, shows a thiophenediyl or benzothiophene diyl, X is chlorine, bromine, iodine, a mesylate group, and arenesulfonate group. When the aromatic compound represented by the formula (1) is reacted in the presence of a base and an aromatic hydrocarbon solvent, a tertiary phosphine or a tertiary phosphite, a nickel salt and an alcohol are added. IV) (R, A, and D are the same as described above.)