Aromatic nitrile compounds or derivatives of same and synthetic method and application thereof

A compound, aryl nitrile technology, applied in the synthesis of aryl nitrile compounds or their derivatives, in the field of aryl nitrile compounds or their derivatives, can solve the problem of poor tolerance of substrate functional groups, not many, complicated operation, etc. problem, to achieve the effect of simple conditions, easy-to-obtain raw materials, and simple reaction equipment

Inactive Publication Date: 2009-12-23
焦宁
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are not many reports on the synthesis method of directly converting aromatic methane into aryl nitrile, although literature (Lücke, B.; Narayana, K.V.; Martin, A.; , K.Adv.Synth.Catal.2004,346,1407.) have done a detailed report on the synthetic method of aromatic nitrile compounds prepared by ammoxidation of aryl methane, but these methods all have the following defects in varying degrees, and need to be improved: 1. The temperature of the reaction is high (300-400°C), and the substrate functional group tolerance is poor; 2. The catalyst needs to be prepared, and the operation of the reaction is complicated

Method used

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  • Aromatic nitrile compounds or derivatives of same and synthetic method and application thereof
  • Aromatic nitrile compounds or derivatives of same and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment 1 4-methoxybenzonitrile

[0027] Take a reaction tube, add 6.2 mg of copper sulfate, 64 mg of 4-methoxytoluene, 44 mg of sodium azide, 175 mg of iodobenzene acetate, and 4 ml of acetonitrile under the protection of nitrogen, and stir at room temperature for two hours. Sodium nitride (44mg×2) and iodobenzene acetate (175mg×2) were added every two hours. After the reaction was completed, it was filtered, the solvent was removed, and 47mg of pure product was obtained by column chromatography with a yield of 71%.

[0028] IR: (KBr)ν max 2969, 2924, 2854, 2219, 1606, 1510, 1461, 1260, 1176, 1024, 832cm -1 ; 1 H NMR (CDCl 3 , 300MHz): δ=7.51(d, J=8.9Hz, 2H), 6.87(m, J=8.9Hz, 2H), 3.78(s, 3H); 13 C NMR (CDCl 3 , 75MHz): δ=162.8, 133.9, 119.2, 114.7, 103.9, 55.5ppm; MS (70eV): m / z (%): 133.1 (M + , 100).

Embodiment 24

[0029] The preparation of embodiment 24-methoxybenzonitrile

[0030] Take a reaction tube, add 6.2 mg of copper sulfate, 64 mg of 4-methoxytoluene, 130 mg of sodium azide, 515 mg of iodobenzene acetate, and 4 ml of acetonitrile under nitrogen protection, and stir at room temperature. After the reaction is completed, filter and remove the solvent , 34 mg of pure product was obtained by column chromatography with a yield of 53%.

[0031] IR: (KBr)ν max 2969, 2924, 2854, 2219, 1606, 1510, 1461, 1260, 1176, 1024, 832cm -1 ; 1 H NMR (CDCl 3 , 300MHz): δ=7.51(d, J=8.9Hz, 2H), 6.87(m, J=8.9Hz, 2H), 3.78(s, 3H); 13 C NMR (CDCl 3 , 75MHz): δ=162.8, 133.9, 119.2, 114.7, 103.9, 55.5ppm; MS (70eV): m / z (%): 133.1 (M + , 100).

Embodiment 3

[0032] The preparation of embodiment 3 4-ethoxybenzonitrile

[0033] Take a reaction tube, add 6.2 mg of copper sulfate, 69 mg of 4-ethoxytoluene, 44 mg of sodium azide, 175 mg of iodobenzene acetate, and 4 ml of acetonitrile under nitrogen protection, and stir at room temperature for two hours, and then stack the other two Sodium nitride (44mg×2) and iodobenzene acetate (175mg×2) were added every two hours. After the reaction was completed, it was filtered, the solvent was removed, and 48mg of pure product was obtained by column chromatography with a yield of 65%.

[0034] IR: (KBr)ν max 2981, 2220, 1605, 1507, 1260, 1172, 1039, 845, 808cm -1 ; 1 H NMR (CDCl 3 , 300MHz): δ=7.57(d, J=9.2Hz, 2H), 6.93(d, J=9.2Hz, 2H), 4.08(q, J=7.0Hz, 2H), 1.44(t, J=7.0Hz ,3H); 13 CNMR (CDCl 3, 75MHz): δ=162.2, 133.9, 119.3, 115.1, 103.6, 63.9, 14.5ppm; HRMSm / z (ESI) calcd for C 9 h 9 NO(M+H) + : 148.0757, found 148.0753.

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PUM

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Abstract

The invention discloses aromatic nitrile compounds or derivatives of same and a synthetic method and an application thereof and the synthetic method of aromatic nitrile compounds or derivatives of same comprises the following steps: using copper or copper compound as auxiliary agent, mixing arylmethane compound, sodium azide and organic solvent to perform aryl methyl cyanation reaction under the action of oxidant and obtaining the finished product. In the method of the invention, copper or copper compound is firstly used as auxiliary agent and arylmethane compound and sodium azide are reactedto prepare aromatic nitrile compounds by adopting iodobenzene acetate as oxidant. The synthetic method of the invention has the advantages of high yield, simple conditions, accessible raw materials, simple reaction equipments, easy realization of industrialized production and the like.

Description

technical field [0001] The invention relates to aryl nitrile compounds or derivatives thereof, and also relates to a synthesis method of aryl nitrile compounds or derivatives thereof, belonging to the field of aryl nitrile compounds. Background technique [0002] Aryl nitriles are a class of biologically active molecular fragments that are widely present in drugs and organisms. The construction of aryl nitriles has always been a research direction that people are more interested in, and a large number of literatures have reported a variety of construction methods of aryl nitriles. However, there are not many reports on the synthesis method of directly converting aromatic methane into aryl nitrile, although literature (Lücke, B.; Narayana, K.V.; Martin, A.; , K.Adv.Synth.Catal.2004,346,1407.) have done a detailed report on the synthetic method of aromatic nitrile compounds prepared by ammoxidation of aryl methane, but these methods all have the following defects in varying ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/54C07C255/57C07F7/18C07C271/28C07C255/50C07C253/00C07C269/06
Inventor 焦宁周旺张亮仁
Owner 焦宁
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