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Method for preparing aryl nitrile by aryl halogenide

An aryl halide and aryl nitrile technology, which is applied in the field of preparing aryl nitrile, can solve the problems of high toxicity of cyanating reagents, complicated separation and purification, and difficult to obtain raw materials, and achieves simple steps, good solubility, and easy products. Effect

Active Publication Date: 2013-01-16
ZHEJIANG UNIV
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  • Summary
  • 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, 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, 52...

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 by aryl halogenide. The method includes that the aryl halogenide and benzonitrile with a molar ratio of 1:1.5 are added in a reactor, an appropriate quantity of copper salt reagent is added to obtain a mixture, the mixture is stirred and heated in an organic solvent, under the air or oxygen condition, the mixture is reacted for 8-16 hours at the temperature from 80 DEG C to 130 DEG C to obtain a product of the aryl nitrile, and the aryl halogenide is aryl iodine or aryl bromide. Compared with traditional methods for preparing the aryl nitrile by the aryl halogenide, the method for preparing the aryl nitrile by the aryl halogenide has the advantages that a common organic reagent of benzonitrile is utilized as a cyaniding raw material, the cyaniding raw material source range is wide, the cyaniding raw material is relatively safe and has a good dissolubility in the organic solvent, the whole preparation steps are simple and convenient, the operation is simple, the productivity is high, metal cyanides with serious toxicity are prevented from being used, metal catalysts are cheap and easy to obtain, and the product is easy to separate and purify.

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 peop...

Claims

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Application Information

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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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