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Synthesis method of 2-(5-methylbenzofuran-2-yl)benzonitrile

A synthesis method, the technology of benzonitrile, which is applied in the direction of organic chemistry, can solve the problems of no suitable industrial synthesis method, and achieve the effect of reasonable reaction process design, easy reaction and short route

Pending Publication Date: 2019-09-20
武汉药明康德新药开发有限公司
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Problems solved by technology

Mainly solve the technical problem that there is no suitable industrial synthesis method at present

Method used

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  • Synthesis method of 2-(5-methylbenzofuran-2-yl)benzonitrile
  • Synthesis method of 2-(5-methylbenzofuran-2-yl)benzonitrile

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Embodiment 1

[0012] Compound 2 (25.04 g, 184 mmol) was dissolved in N,N dimethylformamide (180 mL) and ethanol (90 mL), then sodium ethoxide (10.8 g, 199 mmol) and compound 1 (35 g , 179 mmol, ), stirred under nitrogen atmosphere, then reacted at 90°C for 3 hours, TLC (petroleum ether / ethyl acetate volume ratio = 5 / 1) showed that the reaction was complete. Then, concentrated to remove ethanol in the solvent. Add water (90 mL) to the mixture, and then filter to obtain the crude product. The crude product is subjected to column chromatography (gradient elution: petroleum ether ~ petroleum ether / ethyl acetate volume ratio = 100 / 1 ~ 20 / 1) to obtain the pure product Compound 3 (25 g, 107 mmol). Yield 60.3%.

[0013] 1 DMSO δ= 7.79~7.70 (m, 3H), 7.60~7.54 (m, 3H), 7.30~7.14 (m, 2 H), 2.34 (3, 3H).

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Abstract

The invention relates to a synthesis method of 2-(5-methylbenzofuran-2-yl)benzonitrile. The synthesis method mainly solves the technical problem that an industrial synthesis method does not exist at present. The preparation method comprises a one-step reaction, wherein a compound 1 and a compound 2 are subjected to a reaction in a solvent N,N-dimethylformamide and ethanol under the action of sodium ethoxide to obtain a final compound 3. The reaction equation is shown in the specification.

Description

technical field [0001] The present invention relates to the synthetic method of compound 2-(5-methylbenzofuran-2-yl)benzonitrile. Background technique [0002] Compound 2-(5-methylbenzofuran-2-yl)benzonitrile (143381-79-7) and related derivatives are widely used in medicinal chemistry and organic synthesis. At present, there are few reports on the synthesis methods of 2-(5-methylbenzofuran-2-yl)benzonitrile. Therefore, it is necessary to develop a synthetic method that is easy to obtain raw materials, easy to operate, easy to control the reaction, suitable for overall yield, and suitable for industrial production. Contents of the invention [0003] The purpose of the invention is to develop a kind of having raw material to be easy to get, easy to operate, easy to control reaction, the synthetic method of 2-(5-methylbenzofuran-2-yl) benzonitrile that yield is higher. It mainly solves the technical problem that there is no suitable industrial synthesis method at present. ...

Claims

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Application Information

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IPC IPC(8): C07D307/81C07D307/79
CPCC07D307/81C07D307/79
Inventor 毛晶王密杨云龙刘爽汪永生陈冬枝庞洲张宏伟于凌波马汝建
Owner 武汉药明康德新药开发有限公司
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