Method for preparing aryl nitrile by aryl halogenide

A technology of aryl halides and aryl nitriles, which is applied in the field of preparation of aryl nitriles, can solve the problems of high toxicity of cyanide reagents, complicated separation and purification, and difficult availability of raw materials, and achieve simple steps, good solubility, and easy products Effect

Active Publication Date: 2014-08-06
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the defects of the existing method for preparing aryl nitriles from aryl halides, such as cumbersome steps, high toxicity of cyanation reagents, difficult acquisition of raw materials, complicated separation and purification, and low product yield, and provide a simple and fast , mild and efficient, easy to obtain safe raw materials, easy to operate, easy to purify the method for preparing aryl nitriles from aryl halides

Method used

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  • Method for preparing aryl nitrile by aryl halogenide
  • Method for preparing aryl nitrile by aryl halogenide
  • Method for preparing aryl nitrile by aryl halogenide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The method for preparing 4-methoxybenzonitrile by 4-iodoanisole and phenylacetonitrile

[0019]

[0020] The following steps are adopted: add 0.117 grams of p-iodoanisole in the above reaction formula to a 20ml reaction test tube, add 0.088 grams (1.5 equivalents) of phenylacetonitrile, add 0.072 grams (1 equivalents) of cuprous oxide, and add N,N-dimethyl 2 ml of methyl formamide, heated to 130° C., and reacted under air condition for 8 hours. Then cool to room temperature, pour the reaction mother liquor into 15ml of water, extract three times with dichloromethane (3x5ml), combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent by rotary evaporation. and then separated by column chromatography. 0.061 g of white powdery solid was obtained with a yield of 92%. 1 H NMR (400 MHz, CDCl 3 ): δ 7.59 (d, J = 8.6 Hz, 2H), 6.96 (d, J = 8.6 Hz, 2H), 3.86 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 163.1, 134.2, 119.5, 115.0, 104.2, 55.8. EIM...

Embodiment 2

[0022] The method for preparing methyl 4-cyanobenzoate by methyl 4-iodobenzoate and phenylacetonitrile

[0023]

[0024] The following steps are adopted: add 0.131 grams of methyl p-iodobenzoate in the above reaction formula to a 20 ml reaction test tube, add 0.088 grams (1.5 equivalents) of phenylacetonitrile, add 0.072 grams (1 equivalents) of cuprous oxide, and add dimethyl sulfoxide 2 ml, heated to 130°C, and reacted under air conditions for 16 hours. Then cool to room temperature, pour the reaction mother liquor into 15ml of water, extract three times with dichloromethane (3x5ml), combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent by rotary evaporation. and then separated by column chromatography. 0.069 g of white powdery solid was obtained with a yield of 86%. 1 H NMR (400 MHz, CDCl 3 ): δ 8.15 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 8.4 Hz, 2H), 3.97 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ): δ 165.4, 133.9, 132.2, 130.0, 117.9, 116.3...

Embodiment 3

[0026] Method for preparing 3-cyanoindole from N-methoxyacyl-3-iodoindole and phenylacetonitrile

[0027]

[0028] The following steps are adopted: add 0.151 grams of N-methoxyl-3-iodoindole in the above reaction formula to a 20ml reaction test tube, add 0.088 grams (1.5 equivalents) of phenylacetonitrile, add 0.072 grams (1 equivalents) of cuprous oxide, and add 2 ml of N-methylpyrrolidone was heated to 130° C. and reacted under air conditions for 16 hours. Then cool to room temperature, pour the reaction mother liquor into 15ml of water, extract three times with dichloromethane (3x5ml), combine the organic phases, dry over anhydrous sodium sulfate, and remove the solvent by rotary evaporation. and then separated by column chromatography. 0.046 g of white powdery solid was obtained with a yield of 65%. 1 H NMR (400 MHz, CDCl 3 ): δ 8.80 (br, 1H), 7.80–7.74 (m, 2H), 7.49 (d, J = 7.6 Hz, 1H), 7.37–7.29 (m, 2H). 13 C NMR (125 MHz, d 6 -DMSO): δ 135.9, 135.1, 127.3, 124...

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Abstract

The invention discloses a method for preparing aryl nitrile from aryl halides. The specific reaction steps are to put aryl halides and benzyl cyanides with a molar ratio of 1:1.5 into the reactor, add 1 equivalent of copper salt reagent, stir and heat in an organic solvent, and heat the mixture at 80 to 130°C under air or oxygen conditions. Under reaction for 8 to 16 hours, the product of aryl nitrile is obtained, and the aryl halide is aryl iodide or aryl bromide. With respect to the existing method for preparing aryl nitrile from aromatic halides, the present invention adopts common organic reagent benzyl cyanide as cyanide raw material, corresponding to the traditional way of preparing aryl nitrile by aryl halides, the cyanide raw material Wide range of sources, relatively safe, good solubility in organic solvents, simple overall preparation steps, simple operation, high yield, avoiding the use of toxic metal cyanides, cheap and easy-to-obtain metal catalysts, and easy separation and purification of products.

Description

technical field [0001] The present invention relates to a method for preparing aryl nitriles from aryl halides. Background technique [0002] Aryl nitriles are a class of very useful and important compounds and intermediates, which have very important applications in organic synthesis and various medicines. Such as for the preparation of synthetic tetrazole ( Chemistry of the Cyano Group ; Rappoport, Z., Ed.; Wiley: London, 1970; Chem. Soc. Rev. , 2011, 40, 5049–5067.). This is based on the fact that the cyano group in aryl nitrile is a group that exists in many drug molecules and that the cyano group is easily converted into other groups, which can be used in many fields such as organic synthesis and then drug synthesis. [0003] Because aryl nitriles have important theoretical significance in their preparation and broad prospects in application, it is very important to develop new methods for preparing aryl nitriles. [0004] The preparation method that previous peopl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B43/08C07C253/14C07C255/54C07C255/57C07D209/42C07C255/50C07C255/60C07C255/52
Inventor 吕萍王彦广温俏冬金积松
Owner ZHEJIANG UNIV
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