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Synthesis method of benzonitrile compounds

A synthesis method and technology of benzonitrile, which is applied in the field of preparation of benzonitrile compounds, can solve problems such as high reaction temperature, cumbersome and complicated operation, and achieve the effects of easy-to-obtain raw materials, mild reaction temperature and simple operation

Active Publication Date: 2018-01-30
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this method is that temperature of reaction is higher, and operation is loaded down with trivial details and has only electron-donating substituent tolerance better; (2) take tert-butyl nitrite as nitrogen source, synthesize benzonitrile compound (example: Uttam Dutta, David W. Lupton, and Debabrata Maiti, Org. Lett. 2016, 18, 860)
The disadvantage of this method is that tert-butyl nitrite is unstable and explosive at high temperature, and the operation is complicated and requires inert gas protection.

Method used

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  • Synthesis method of benzonitrile compounds
  • Synthesis method of benzonitrile compounds
  • Synthesis method of benzonitrile compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: take phenylacetylene as raw material, synthesize benzonitrile

[0025]

[0026] Add 51mg (0.50mmol) of phenylacetylene, 154mg (1mmol) of silver nitrite, and 133.5mg (1mmol) of N-chlorosuccinimide into a 10mL pressure-resistant sealed container in sequence, and then add 5mL of acetonitrile. The mixture was stirred and reacted at room temperature, followed by TLC detection, and the reaction was completed in 8 hours. The reaction solution was diluted with 10mL of dichloromethane, filtered to obtain the clear liquid, and the organic solvent was evaporated to purify with a silica gel column, and then column chromatography ( (Petroleum ether / ethyl acetate mixed solution with a volume ratio of 100:1 was used as eluent) for separation, the eluate containing the target product was collected and the solvent was evaporated to obtain 35 mg of colorless oily liquid benzonitrile (68% yield).

[0027] Colorless oily liquid; IR(neat):2229(C≡N)cm -1 ; 1 H NMR (CDCl 3...

Embodiment 2

[0028] Embodiment 2: take phenylacetylene as raw material, synthesize benzonitrile

[0029]

[0030] Add 51mg (0.50mmol) of phenylacetylene, 231mg (1.5mmol) of silver nitrite, and 200.3mg (1.5mmol) of N-chlorosuccinimide into a 10mL pressure-resistant sealed container in sequence, and then add 2.5mL of acetonitrile. The mixture was stirred and reacted at room temperature, followed by TLC detection, and the reaction was completed in 4 hours. The reaction solution was diluted with 10 mL of dichloromethane, filtered to obtain the clear liquid, and the organic solvent was evaporated to purify with a silica gel column, and then column chromatography ( (Petroleum ether / ethyl acetate mixed solution with a volume ratio of 100:1 was used as eluent) for separation, the eluate containing the target product was collected and the solvent was evaporated to obtain 33.5 mg of colorless oily liquid benzonitrile (65% yield).

[0031] Colorless oily liquid; IR(neat):2229(C≡N)cm -1 ; 1 H NMR...

Embodiment 3

[0032] Embodiment 3: take phenylacetylene as raw material, synthesize benzonitrile

[0033]

[0034] Add 51mg (0.50mmol) of phenylacetylene, 154mg (1mmol) of silver nitrite, and 178mg (1mmol) of N-bromosuccinimide into a 10mL pressure-resistant sealed container in sequence, and then add 5mL of nitromethane. The mixture was stirred and reacted at 0°C, followed by TLC detection, and the reaction was completed after 12 hours. The reaction solution was diluted with 10 mL of dichloromethane, and the clear liquid was obtained by filtration. After the organic solvent was evaporated, it was purified with a silica gel column, and then column chromatography (with the mixed solution of petroleum ether / ethyl acetate volume ratio 100:1 as the eluent) separation, collecting the eluent containing the target product and evaporating the solvent to obtain 30.9 mg of colorless oily liquid benzonitrile (60% yield) .

[0035] Colorless oily liquid; IR(neat):2229(C≡N)cm -1 ; 1 H NMR (CDCl 3 ...

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Abstract

The invention provides a preparation method of benzonitrile compounds. The preparation method comprises the steps: carrying out a reaction in an organic solvent at 0-50 DEG C for 4-12h under the action of an oxidant by taking phenylacetylene as shown in the formula (I) and a derivative of phenylacetylene as raw materials and nitrite as a nitrogen source, and separating and purifying the obtained reaction liquid to prepare the benzonitrile compound as shown in the formula (II); and the amount-of-substance ratio of the nitrogen source to phenylacetylene as shown in the formula (I) and the derivative of phenylacetylene is (1-3):1. The preparation method is simple and available in raw material, mild in reaction condition, good in functional group tolerance, simple in operation and environment-friendly so as to be a novel method for synthesizing benzonitrile containing various substituent groups.

Description

technical field [0001] The invention relates to a preparation method of benzonitrile compounds. Background technique [0002] Benzonitrile compounds are an important class of organic compounds, mainly used as intermediates for advanced coatings such as benzomelamine, as well as intermediates for the synthesis of pesticides, aliphatic amines, and benzoic acid, and can be used as nitrile rubbers, resins, polymers, etc. solvents for substances and paints, etc. The traditional methods for preparing benzonitriles are mainly through Rosenmund-von Braun reaction and Sandmeyer reaction. However, the toxic CuCN is used as a nitrogen source in the reaction process, which greatly limits its development space. In addition, there are benzoic acid method, amine oxidation method, toluene cyanation method, transition metal-catalyzed coupling reaction to synthesize benzonitrile compounds. However, some of these methods have high reaction temperatures and harsh conditions; some use explosi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/00C07C255/50C07C255/54C07D307/79
Inventor 刘运奎张剑鲍汉扬
Owner ZHEJIANG UNIV OF TECH
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