CN115490613B - Preparation method of aromatic nitrile compound - Google Patents

Preparation method of aromatic nitrile compound Download PDF

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CN115490613B
CN115490613B CN202211079018.6A CN202211079018A CN115490613B CN 115490613 B CN115490613 B CN 115490613B CN 202211079018 A CN202211079018 A CN 202211079018A CN 115490613 B CN115490613 B CN 115490613B
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aromatic nitrile
carboxylic acid
nitrile compound
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CN115490613A (en
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张国富
缪慧慧
关晨飞
丁成荣
吕井辉
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Zhejiang University of Technology ZJUT
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    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
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Abstract

The invention discloses a preparation method of an aromatic nitrile compound, which comprises the following steps: the carboxylic acid compound is used as a raw material, zinc cyanide, pivalic anhydride, a metal catalyst, a ligand and a solvent are firstly added, the reaction is carried out for 8 to 16 hours at the temperature of 120 to 180 ℃, and then the reaction liquid is cooled to the room temperature, so that the aromatic nitrile compound shown in the formula (II) is prepared; the invention uses the pivalic anhydride which has stable structure and easy storage as the additive, efficiently promotes the carboxylic acid to generate the anhydride intermediate, and simultaneously uses the zinc cyanide which is cheap, easy to obtain and environment-friendly as the cyanide source. Avoiding the use of other dangerous reagents which are extremely toxic and unstable, and obtaining the corresponding aromatic nitrile compound with better yield. The operation process is simple, and the target product can be obtained only by column chromatography separation and purification in the post-treatment.

Description

Preparation method of aromatic nitrile compound
Field of the art
The invention relates to a preparation method of an aromatic nitrile compound, in particular to a preparation method for generating the nitrile compound by decarbonylation and cyanidation under the catalysis of metal by taking zinc cyanide as a cyanide source and pivalic anhydride as an additive and taking carboxylic acid compound as a substrate.
(II) background art
Aromatic nitriles are ubiquitous bioactive organic compounds, so they are often used as pharmaceuticals, agrochemicals and bioactive natural products. Conventional methods for synthesizing aromatic nitriles are Sandmeyer and Rosenmund von Braun, but they have disadvantages in that they require the use of toxic reagents or under high temperature conditions to achieve and a narrow substrate range. Thus, so far, it remains an active topic on organic chemical synthesis how to develop a novel and effective method to build aromatic nitriles. In recent years, the use of transition metal catalyzed nucleophilic cyanidation of aryl halides or pseudohalides with various CN sources to produce aryl nitrile compounds has been an effective process. In contrast, carboxylic acid functionalities are ubiquitous, stable and readily available, and are widely used in organic synthesis. Many strategies have been developed by scientists to use carboxylic acid derivatives as reactive groups to form c—c bonds by decarboxylation or decarbonylation. At the same time, metal-catalyzed decarbonylation reactions are increasingly being usedSynthesizing aromatic nitrile. For example, the szostank group of topics has successfully developed the decarbonylation cyanidation of palladium-catalyzed amides to synthesize various aryl nitriles [ org.]The method comprises the steps of carrying out a first treatment on the surface of the Rueping et al found that a phenolic ester or amide was catalyzed with Zn (CN) by nickel 2 An efficient process for decarbonylcyanation to obtain aryl nitriles [ org.]The method comprises the steps of carrying out a first treatment on the surface of the Subsequently, the Nishihara group used nickel to catalyze the decarbonylation of acid chlorides synthesized a series of nitrile compounds under neutral conditions [ org.]. However, these processes have disadvantages, such as the need to pre-synthesize carboxylic acid derivatives or the use of unstable and odorous starting acid chlorides.
(III) summary of the invention
Aiming at the defects existing in the prior art, the invention provides a novel method for synthesizing the aromatic nitrile compound efficiently, environmentally-friendly, economically and rapidly.
The technical scheme adopted by the invention is as follows:
the invention provides a preparation method of an aromatic nitrile compound shown in a formula (II), which comprises the following steps:
taking carboxylic acid compounds shown in a formula (I) as raw materials, adding zinc cyanide, pivalic anhydride, a metal catalyst, a ligand and an organic solvent, reacting for 8-16 hours at 120-180 ℃ in a nitrogen atmosphere, and performing post-treatment on a reaction solution to obtain aromatic nitrile compounds shown in a formula (II);
the metal catalyst is one of the following: palladium chloride, palladium trifluoroacetate, palladium acetylacetonate, palladium acetate or palladium bis dibenzylidene acetonate;
the ligand is one of the following: bis (diphenylphosphine) methane (Dppm), 1, 4-bis (diphenylphosphine) butane (Dppb), 1, 5-bis (diphenylphosphine) pentane (dppe), 1' -bis (diphenylphosphine) ferrocene (Dppf), 4, 5-bis (diphenylphosphine) -9,9-dimethylxanthenes (Xantphos), bis (2-diphenylphosphino) phenyl ethers (DPEPhos) or triphenylphosphine (PPh) 3 )；
The organic solvent is one of the following: toluene, 1, 4-dioxane, dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, acetonitrile, ethyl acetate or N-methylpyrrolidone;
r in the formula (I) is aryl, C1-C6 linear or branched alkyl, and R in the formula (II) is the same as R in the formula (I).
Preferably, R in the formula (I) is 4-acenyl, 4-phenyl, 4-methoxy, 4-methyl formate or 4-acetyl.
Further, the ratio of the amount of zinc cyanide to the amount of the carboxylic acid compound represented by the formula (I) is 1 to 5:1, preferably 1 to 3:1, more preferably 1.5:1. The volume amount of the organic solvent is 1 to 10mL/mmol, preferably 5mL/mmol, based on the amount of the carboxylic acid compound represented by the formula (I). The ratio of the amount of the pivalic anhydride to the carboxylic acid compound shown in the formula (I) is 1-5: 1, preferably 1.5:1. the ratio of the amount of the metal catalyst to the amount of the carboxylic acid compound represented by the formula (I) is 0.01 to 0.3:1, preferably 0.05:1. The ratio of the amounts of the substances of the carboxylic acid compounds shown in the formula (I) is 0.01-0.6: 1, preferably 0.05:1.
Further, the reaction temperature is preferably 150 to 170℃and the reaction time is 12 hours.
Further, the post-treatment method of the reaction liquid comprises the following steps: after the reaction, the reaction solution is cooled to room temperature and 10 to 30 times of the volume of CH is used 2 Cl 2 Diluting, filtering, concentrating the filtrate to dryness to obtain a crude product; dissolving the crude product with dichloromethane, adding silica gel powder, uniformly mixing, concentrating to dryness, loading the crude product into a silica gel chromatographic column by adopting a dry method, and petroleum ether with the volume ratio of 10-30:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 10-30:1: thin-layer chromatography monitoring is carried out by taking ethyl acetate as developing agent, eluent with Rf=0.3-0.7 is collected, and the eluent is concentrated to be dryObtaining the aromatic nitrile compound shown in the formula (II).
Preferably, the particle size of the silica gel powder is 300-400 meshes, the diameter of the silica gel chromatographic column is 3cm, the height of the silica gel chromatographic column is 30cm, and the height of the packed column is 16cm.
Preferably, the volume amount of the dichloromethane is 0.1-1.0mL/mg, preferably 0.15-0.25mL/mg, calculated by the mass of the crude product; the mass ratio of the crude product to the silica gel powder is 1:50-80.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention uses the pivalic anhydride which has stable structure and easy storage as the additive to efficiently promote the carboxylic acid to generate the anhydride intermediate.
2. The invention uses zinc cyanide which is cheap and easy to obtain and is environment-friendly as a cyanide source.
3. Zinc cyanide, pivalic anhydride avoid the use of other dangerous reagents that are extremely toxic and unstable.
4. The substrate applicability is wide, and the yield of the aromatic nitrile compound is 40-97%.
5. Solves the tedious problem of the prior synthesis and purification of carboxylic acid derivatives as raw materials, and optimizes the use of tasty and unstable reagents.
6. The operation process is simple, and the target product can be obtained only by column chromatography separation and purification in the post-treatment.
(IV) description of the drawings
FIG. 1 shows the nuclear magnetic resonance hydrogen spectrum (A), the carbon spectrum (B) and the mass spectrum (C) of the compound prepared in example 1.
FIG. 2 shows the nuclear magnetic resonance hydrogen spectrum (A), the carbon spectrum (B) and the mass spectrum (C) of the compound prepared in example 2.
FIG. 3 shows the nuclear magnetic resonance hydrogen spectrum (A), the carbon spectrum (B) and the mass spectrum (C) of the compound prepared in example 3.
FIG. 4 shows the nuclear magnetic resonance hydrogen spectrum (A), the carbon spectrum (B) and the mass spectrum (C) of the compound prepared in example 4.
FIG. 5 shows the nuclear magnetic resonance hydrogen spectrum (A), the carbon spectrum (B) and the mass spectrum (C) of the compound prepared in example 5.
(fifth) detailed description of the invention
The invention will be further described with reference to the following specific examples, but the scope of the invention is not limited thereto: the room temperature of the invention is 25-30 ℃.
Example 1: naphthalene-2-carbonitriles
Into a 25mL Schlenk tube, 0.0344g (0.2 mmol) of 2-naphthoic acid represented by formula (I-1), 0.0235g (0.2 mmol) of zinc cyanide, 0.0559g (0.3 mmol) of pivalic anhydride, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos), 1mL of 1, 4-dioxane solvent were sequentially added; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and was then cooled to room temperature with CH 2 Cl 2 (10 mL) was diluted, filtered, and the filtrate was concentrated to dryness to give 52.5mg of crude product.
After 52.5mg of crude product is dissolved by 10mL of dichloromethane, 3g of silica gel powder (with the particle size of 300-400 meshes) is added, and after being uniformly mixed, the mixture is concentrated to dryness, and a silica gel chromatographic column (with the height of 30cm, the diameter of 3cm and the column height of 16 cm) is packed by a dry method, and petroleum ether with the volume ratio of 20:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 20:1: thin-layer chromatography monitoring is carried out by using ethyl acetate as developing agent, eluent with Rf=0.45 is collected, and the eluent is concentrated to be dry, thus obtaining 27.6mg of naphthalene-2-carbonitrile shown in the formula (II-1) with the yield of 90%. The nuclear magnetic resonance hydrogen spectrum is shown as A in figure 1, the nuclear magnetic resonance carbon spectrum is shown as B in figure 1, and the mass spectrum is shown as C in figure 1.
Nuclear magnetic resonance hydrogen spectrum (400 MHz, CDCl) 3 )δ8.19(s,1H),7.88(t,J＝7.1Hz,3H),7.68–7.53(m,3H).
Nuclear magnetic resonance carbon spectrum (101 MHz, CDCl) 3 )δ134.65,134.17,132.24,129.23,129.09,128.44,128.09,127.70,126.34,119.31,109.35.
Mass spectrometry: HRMS (EI) calcd for C 11 H 7 N:153.0578；Found:153.0583.
Comparative example 1: naphthalene-2-carbonitriles
Into a 25mL Schlenk tube, 0.0344g (0.2 mmol) of 2-naphthoic acid represented by formula (I-1), 0.0235g (0.2 mmol) of zinc cyanide, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos), 1mL of 1, 4-dioxane solvent were sequentially added; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After completion of the reaction, the reaction mixture was examined, and no naphthalene-2-carbonitrile was produced after the examination, indicating that the addition of pivalic anhydride was necessary and useful in the reaction.
Comparative example 2: naphthalene-2-carbonitriles
0.0198g (0.2 mmol) of trimethylnitrile silane in example 1 was used in place of zinc cyanide, and the reaction solution was examined under the same conditions and in the same manner as in example 1 to obtain no product.
Comparative example 3: naphthalene-2-carbonitriles
The reaction solution was examined in example 1 under the same conditions and operation as in example 1 except that 0.0737g (0.2 mmol) of potassium ferrocyanide was used instead of zinc cyanide, and no product was produced.
Example 2: [1,1' -biphenyl ] -4-carbonitrile
0.0396g (0.2 mmol) of biphenyl-4-carboxylic acid of formula (I-2), 0.0235g (0.2 mmol) of zinc cyanide, 0.0559g (0.3 mmol) of pivalic anhydride, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos) and 1mL of 1, 4-dioxane solvent were sequentially added to a 25mL Schlenk's tube; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and was then cooled to room temperature with CH 2 Cl 2 (10 mL) was diluted, filtered, and the filtrate was concentrated to dryness to give 65.3mg of crude product.
After 65.3mg of crude product is dissolved by 10mL of dichloromethane, 5g of silica gel powder (300-400 meshes) is added and mixed uniformly, and then concentrated to be dry, the crude product is loaded on a silica gel chromatographic column (column diameter is 3cm, height is 30cm, column loading height is 16 cm) by a dry method, and petroleum ether is added according to a volume ratio of 20:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 20:1: thin layer chromatography monitoring is carried out by using ethyl acetate as developing agent, and eluent with Rf=0.63 is collected to obtain 33.0mg of [1,1' -biphenyl ] -4-nitrile shown in formula (II-2), and the yield is 92%. The nuclear magnetic resonance hydrogen spectrum is shown as A in figure 2, the nuclear magnetic resonance carbon spectrum is shown as B in figure 2, and the mass spectrum is shown as C in figure 2.
Nuclear magnetic resonance hydrogen spectrum (400 MHz, CDCl) 3 )δ7.71(q,J＝8.5Hz,4H),7.62–7.57(m,2H),7.49(t,J＝7.3Hz,2H),7.46–7.40(m,1H).
Nuclear magnetic resonance carbon spectrum (101 MHz, CDCl) 3 )δ145.76,139.25,132.70,129.22,128.77,127.83,127.33,119.08,110.97.
Mass spectrometry: HRMS (EI) calcd for C 13 H 9 N:179.0735；Found:179.0738.
Example 3: 4-Cyanobenzoic acid methyl ester
0.0360g (0.2 mmol) of monomethyl terephthalate of formula (I-3), 0.0235g (0.2 mmol) of zinc cyanide, 0.0559g (0.3 mmol) of pivalic anhydride, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos) and 1mL of 1, 4-dioxane solvent were sequentially added to a 25mL Schlenk's tube; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and was then cooled to room temperature with CH 2 Cl 2 (10 mL) was diluted, filtered, and the filtrate was concentrated to dryness to give 58.3mg of crude product.
58.3mg of crude product is dissolved by 10mL of dichloromethane, 3g of silica gel powder (300-400 meshes) is added, and after being uniformly mixed, the mixture is concentrated to be dry, and the mixture is loaded on a silica gel chromatographic column (column diameter is 3cm, height is 30cm, column loading height is 16 cm) by a dry method, and petroleum ether is added according to a volume ratio of 10:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 10:1: thin layer chromatography monitoring is carried out by using ethyl acetate as developing agent, and eluent with Rf=0.56 is collected to obtain 25.8mg of 4-cyanobenzoic acid methyl ester shown in formula (II-3), and the yield is 80%. The nuclear magnetic resonance hydrogen spectrum is shown as A in figure 3, the nuclear magnetic resonance carbon spectrum is shown as B in figure 3, and the mass spectrum is shown as C in figure 3.
Nuclear magnetic resonance hydrogen spectrum (400 MHz, CDCl) 3 )δ8.18–8.02(m,2H),7.78–7.61(m,2H),3.92(s,3H).
Nuclear magnetic resonance carbon spectrum (101 MHz, CDCl) 3 )δ165.42,133.91,132.24,130.09,117.97,116.36,52.74.
Mass spectrometry: HRMS (EI) calcd for C 9 H 7 NO 2 :161.0477；Found:161.0485.
Example 4: 4-methoxybenzonitrile
Into a 25mL Schlenk tube, 0.0304g (0.2 mmol) of 4-methoxybenzoic acid represented by formula (I-4), 0.0235g (0.2 mmol) of zinc cyanide, 0.0559g (0.3 mmol) of pivalic anhydride, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos), 1mL of 1, 4-dioxane solvent were sequentially added; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and was then cooled to room temperature with CH 2 Cl 2 (10 mL) was diluted, filtered, and the filtrate was concentrated to dryness to give 48.9mg of crude product.
48.9mg of crude product is dissolved by 10mL of dichloromethane, 3g of silica gel powder (300-400 meshes) is added, and after being uniformly mixed, the mixture is concentrated to be dry, and the dry sample is loaded on a silica gel chromatographic column (the diameter of the column is 3cm, the height of the column is 30cm, and the loading height of the column is 16 cm), and petroleum ether is added according to the volume ratio of 30:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 30:1: thin layer chromatography monitoring is carried out by using ethyl acetate as developing agent, and eluent with Rf=0.65 is collected to obtain 24.0mg of 4-methoxybenzonitrile shown in formula (II-4) with the yield of 90%. The nuclear magnetic resonance hydrogen spectrum is shown as A in figure 4, the nuclear magnetic resonance carbon spectrum is shown as B in figure 4, and the mass spectrum is shown as C in figure 4.
Nuclear magnetic resonance hydrogen spectrum (400 MHz, CDCl) 3 )δ7.62–7.55(m,2H),6.98–6.91(m,2H),3.85(s,3H).
Nuclear magnetic resonance carbon spectrum (101 MHz, CDCl) 3 )δ162.86,134.01,119.27,114.77,103.94,55.58.
Mass spectrometry: HRMS (EI) calcd for C 8 H 7 NO:133.0528；Found:133.0530.
Example 5: 4-Acetylbenzonitrile
0.0328g (0.2 mmol) of 4-acetylbenzoic acid represented by the formula (I-5), 0.0235g (0.2 mmol) of zinc cyanide, 0.0559g (0.3 mmol) of pivalic anhydride, 0.0022g (0.01 mmol) of palladium acetate, 0.0174g (0.03 mmol) of 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene (Xantphos) and 1mL of 1, 4-dioxane solvent were sequentially added to a 25mL Schlenk's tube; the reaction mixture was placed in a preheated oil bath at 160℃under nitrogen and reacted at 160℃for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and was then cooled to room temperature with CH 2 Cl 2 (10 mL) was diluted, filtered, and the filtrate was concentrated to dryness to give 38.6mg of crude product.
After 38.6mg of crude product is dissolved by 10mL of dichloromethane, 2.5g of silica gel powder (300-400 meshes) is added, and after being uniformly mixed, the mixture is concentrated to dryness, a dry method is adopted for loading a silica gel chromatographic column (the diameter of the column is 3cm, the height of the column is 30cm, the height of the column is 16 cm), and petroleum ether with the volume ratio of 10:1 is adopted: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 10:1: thin layer chromatography monitoring is carried out by using ethyl acetate as developing agent, and eluent with Rf=0.53 is collected to obtain 17.4mg of 4-acetyl benzonitrile shown in formula (II-5), and the yield is 60%. The nuclear magnetic resonance hydrogen spectrum is shown as A in figure 5, the nuclear magnetic resonance carbon spectrum is shown as B in figure 5, and the mass spectrum is shown as C in figure 5.
Nuclear magnetic resonance hydrogen spectrum (400 MHz, CDCl) 3 )δ8.08–7.98(m,2H),7.79–7.70(m,2H),2.62(s,3H).
Nuclear magnetic resonance carbon spectrum (101 MHz, CDCl) 3 )δ196.63,139.91,132.54,128.73,117.97,116.36,26.81.
Mass spectrometry: HRMS (EI) calcd for C 9 H 7 NO:145.0528；Found:145.0534.

Claims (6)

1. A process for the preparation of an aromatic nitrile compound, comprising:
taking carboxylic acid compounds shown in a formula (I) as raw materials, adding zinc cyanide, pivalic anhydride, a metal catalyst, a ligand and an organic solvent, reacting for 8-16 hours at 120-180 ℃ in a nitrogen atmosphere, and performing post-treatment on a reaction solution to obtain aromatic nitrile compounds shown in a formula (II);
the metal catalyst is one of the following: palladium chloride, palladium trifluoroacetate, palladium acetylacetonate, palladium acetate or palladium bis dibenzylidene acetonate;
the ligand is one of the following: bis (diphenylphosphine) methane, 1, 4-bis (diphenylphosphine) butane, 1, 5-bis (diphenylphosphine) pentane, 1' -bis (diphenylphosphine) ferrocene, 4, 5-bis (diphenylphosphine) -9, 9-dimethylxanthene, bis (2-diphenylphosphine) phenyl ether or triphenylphosphine;
the organic solvent is one of the following: toluene, 1, 4-dioxane, dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, acetonitrile, ethyl acetate or N-methylpyrrolidone;
r in the formula (I) is 4-acenyl, 4-phenyl, 4-methoxy, 4-methyl formate and 4-acetyl, and R in the formula (II) is the same as R in the formula (I).
2. The method for producing an aromatic nitrile compound according to claim 1, wherein the ratio of the amount of zinc cyanide to the amount of the carboxylic acid compound represented by the formula (I) is 1 to 5:1, a step of; the volume consumption of the organic solvent is 1-10 mL/mmol based on the amount of carboxylic acid compound substances shown in the formula (I); the ratio of the amount of the pivalic anhydride to the carboxylic acid compound shown in the formula (I) is 1-5: 1, a step of; the ratio of the amount of the metal catalyst to the amount of the carboxylic acid compound represented by the formula (I) is 0.01 to 0.3:1, a step of; the ratio of the amounts of the substances of the carboxylic acid compounds shown in the formula (I) is 0.01-0.6: 1.
3. the method for producing an aromatic nitrile compound according to claim 1, wherein the reaction temperature is 150 to 170℃and the reaction time is 12 hours.
4. The method for producing an aromatic nitrile compound according to claim 1, wherein the method for post-treatment of the reaction liquid is as follows: after the reaction, the reaction solution is cooled to room temperature and 10 to 30 times of the volume of CH is used 2 Cl 2 Diluting, filtering, concentrating the filtrate to dryness to obtain a crude product; dissolving the crude product with dichloromethane, adding silica gel powder, uniformly mixing, concentrating to dryness, loading the crude product into a silica gel chromatographic column by adopting a dry method, and petroleum ether with the volume ratio of 10-30:1: performing silica gel column chromatography by using ethyl acetate as an eluent, and petroleum ether with the volume ratio of 10-30:1: and (3) carrying out thin-layer chromatography monitoring by taking ethyl acetate as a developing agent, collecting eluent with Rf=0.3-0.7, and concentrating the eluent to dryness to obtain the aromatic nitrile compound shown in the formula (II).
5. The method for producing an aromatic nitrile compound according to claim 4, wherein the silica gel powder has a particle size of 300 to 400 meshes, the silica gel column has a diameter of 3cm and a height of 30cm, and the column is packed with 16cm.
6. The process for producing an aromatic nitrile compound according to claim 4, wherein the volume amount of methylene chloride is 0.1 to 1.0mL/mg in terms of the mass of the crude product; the mass ratio of the crude product to the silica gel powder is 1:50-80.
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