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Method for synthesizing aryl nitrile compound from tert-butyl isonitrile

A technology of tert-butyl isonitrile and compound, which is applied in the field of synthesizing aryl nitrile substances, and achieves the effect of reducing reaction cost, low cost and abundant reserves

Pending Publication Date: 2022-03-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using tert-butyl isonitrile as a cyanogen source, the formation of aryl nitrile compounds by cheap metal Ni has not been reported.

Method used

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  • Method for synthesizing aryl nitrile compound from tert-butyl isonitrile
  • Method for synthesizing aryl nitrile compound from tert-butyl isonitrile
  • Method for synthesizing aryl nitrile compound from tert-butyl isonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Under the protection of nitrogen, 0.4mmol (61.2mg) 1-iodonaphthalene, NiBr 2 (1equiv, 87.4mg), sodium tert-butoxide (1equiv, 38.4mg), phosphine ligand dppp (20mol%, 33mg) were added to a 25mL Schlenk tube, 2mL of toluene was added as a solvent, followed by 0.6mmol (49.9mg) tert-Butylisonitrile. Next, the reaction was stirred in an oil bath at 150 °C for 12 hours. After the reaction, cool the reaction solution to room temperature, dilute the reaction solution with 2 mL of ethyl acetate, then add 500 mg of silica gel to the reaction solution, mix well, and rotate to evaporate, use n-hexane: ethyl acetate = 50: 1 to wash through the silica gel column After the target product was obtained, 39.78 mg of pure product was obtained by concentration under reduced pressure in vacuo, with a yield of 65%.

[0025] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ8.24(dq, J=8.3,0.9Hz,1H),8.08(dd,J=8.3,1.2Hz,1H),7.92(td,J=7.7,7.2,1.0Hz,2H),7.70(ddd ,J=8.3,6.9,1.3Hz,1H...

Embodiment 2

[0027]

[0028] Under nitrogen protection, 0.4mmol (240mg) 4-tert-butyl iodobenzene, NiBr 2 (1equiv, 87.4mg), sodium tert-butoxide (1equiv, 38.4mg), phosphine ligand dppp (20mol%, 33mg) were added to a 25mL Schlenk tube, 2mL of toluene was added as a solvent, followed by 0.6mmol (49.9mg) tert-Butylisonitrile. Next, the reaction was stirred in an oil bath at 150 °C for 12 hours. After the reaction, cool the reaction solution to room temperature, dilute the reaction solution with 2 mL of ethyl acetate, then add 500 mg of silica gel to the reaction solution and mix well, then rotate and evaporate, and use n-hexane: ethyl acetate = 80: 1 to wash the reaction solution through a silica gel column. After decompression, the target product was obtained and concentrated under reduced pressure to obtain 43.9 mg of pure product with a yield of 69%.

[0029] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ7.62–7.57(m,2H),7.52–7.47(m,2H),1.34(s,9H).

Embodiment 3

[0031]

[0032] Under nitrogen protection, 0.4mmol (99.6mg) p-nitroiodobenzene, NiBr 2 (1equiv, 87.4mg), sodium tert-butoxide (1equiv, 38.4mg), phosphine ligand dppp (20mol%, 33mg) were added to a 25mL Schlenk tube, 2mL of toluene was added as a solvent, followed by 0.6mmol (49.9mg) tert-Butylisonitrile. Next, the reaction was stirred in an oil bath at 150 °C for 12 hours. After the reaction, cool the reaction solution to room temperature, dilute the reaction solution with 2mL ethyl acetate, then add 500 mg of silica gel to the reaction solution, mix well and then rotatively evaporate, use n-hexane:ethyl acetate=50:1 to conduct After elution, the target product was obtained and concentrated under reduced pressure to obtain 18.4 mg of pure product with a yield of 31%.

[0033] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ8.41–8.35(m,2H),7.96–7.88(m,2H).

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Abstract

The invention relates to a synthesis method of an organic compound, in particular to a method for synthesizing a nitrile substance under the action of nickel by using tert-butyl isocyanate as a cyanation reagent, and the method is characterized in that an iodobenzene compound as shown in a formula I and tert-butyl isocyanide as shown in a formula II are used as raw materials to obtain a nitrile compound as shown in a formula III. The nickel bromide is rich in reserve and low in price, the reaction cost is reduced, the toxicity of the used tert-butyl isocyanide is low, the production difficulty is reduced, and the life safety of production personnel is protected. The method provided by the invention can effectively synthesize various aryl nitrile compounds.

Description

technical field [0001] The invention relates to a method for using tert-butyl isonitrile as a cyanation agent to synthesize aryl nitrile substances under the action of nickel. Background technique [0002] Nitrile compounds are widely used in the synthesis of medicines, insecticides, spices, dyes, electroluminescent materials, polyacrylonitrile and nitrile rubber; meanwhile, nitrile is also a very important intermediate in organic synthesis, which can be easily Conversion to other very useful target compounds, such as amides, carboxylic acids, amines, aldehydes and ketones, etc. Therefore, the preparation and application of nitrile compounds are of great significance in industrial production and theoretical research. [0003] There are many ways to synthesize nitrile compounds, some of which are realized by introducing a cyanide source (cyano ion). In recent years, transition metal-catalyzed (such as Pd, Ni, Cu, Zn, Rh, etc.) carbon-carbon bond construction reactions have ...

Claims

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Application Information

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IPC IPC(8): C07B43/08C07C253/14C07C255/52C07C255/50C07C255/54C07C255/56C07C255/57C07D333/38
CPCC07B43/08C07C253/14C07D333/38C07C255/52C07C255/50C07C255/54C07C255/56C07C255/57
Inventor 周丙伟章治国金红卫刘运奎
Owner ZHEJIANG UNIV OF TECH
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