Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for synthesizing aromaticnitrile

An aromatic nitrile and compound technology, which is applied in the field of synthesizing aromatic nitrile compounds, can solve the problems of serious environmental pollution, harsh reaction conditions, high toxicity of cyanide source, etc., and achieves the effects of safe and simple operation, easy availability and low price.

Active Publication Date: 2015-08-12
SOUTH CHINA UNIV OF TECH
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, some methods use expensive transition metal catalysis (such as palladium, rhodium catalyst) and cyanogen source, some cyanogen sources are highly toxic, serious environmental pollution (such as sodium cyanide or potassium cyanide), and the reaction conditions are relatively harsh

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for synthesizing aromaticnitrile
  • Method for synthesizing aromaticnitrile
  • Method for synthesizing aromaticnitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044]Add 0.3 mmol 4-biphenylboronic acid, 0.6 mmol 2-cyano-3-ethoxy ethyl acrylate, 0.3 mmol cuprous iodide, 2 ml N,N-dimethylformamide to the reaction flask , 0.3 millimoles of tert-butanol peroxide, in the air atmosphere, 130 ° C stirring reaction for 24 hours, stop heating and stirring, cooled to room temperature, vacuum distillation to obtain the crude product, and then separated and purified by column chromatography to obtain the target product , the column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate, wherein the volume ratio between petroleum ether and ethyl acetate is 20:1, and the yield is 72%.

Embodiment 2

[0046] Add 0.3 mmol 4-biphenylboronic acid, 0.6 mmol 2-cyano-3-ethoxy ethyl acrylate, 0.3 mmol cuprous iodide, 2 ml N,N-dimethylformamide to the reaction flask , 0.3 millimoles of tert-butanol peroxide, in the air atmosphere, 100 ° C stirring reaction for 24 hours, stop heating and stirring, cooled to room temperature, vacuum distillation to obtain the crude product, and then separated and purified by column chromatography to obtain the target product , the column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate, wherein the volume ratio between petroleum ether and ethyl acetate is 20:1, and the yield is 30%.

Embodiment 3

[0048] Add 0.3 mmol 4-biphenylboronic acid, 0.6 mmol 2-cyano-3-ethoxy ethyl acrylate, 0.3 mmol cuprous iodide, 2 ml N,N-dimethylformamide to the reaction flask , 0.3 millimoles of tert-butanol peroxide, under air atmosphere, 120 ° C stirring reaction for 24 hours, stop heating and stirring, cooled to room temperature, vacuum distillation to obtain the crude product, and then separated and purified by column chromatography to obtain the target product , the column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate, wherein the volume ratio between petroleum ether and ethyl acetate is 20:1, and the yield is 52%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a method for synthesizing aromaticnitrile. The method comprises the following steps: under the atmosphere of air or oxygen gas, heating to 80-150 DEG C for performing a stirring reaction for 12-48 hours by taking 2-cyan-3-ethoxyl-ethyl acrylate as a cyanogens source, taking phenylboronic acid compounds or halogen compounds as raw materials, taking copper salt as an accelerant, taking peroxide as an oxidant and taking an organic solvent as a solvent; after the reaction is finished, cooling to room temperature, filtering, carrying out reduced pressure distillation and concentration to obtain a crude product; then purifying through column chromatography to obtain an aromaticnitrile compound. The method for synthesizing the aromaticnitrile compound disclosed by the invention is safe and simple to operate, good in functional group adaptation, wide in substrate adaptation and environmentally-friendly, is beneficial to industrial production, and is extensively applied in medicines and organic synthesis; the raw materials are easily obtained and low in price.

Description

technical field [0001] The invention relates to the technical fields of medicine and organic chemical synthesis, in particular to a method for synthesizing aromatic nitrile compounds. Background technique [0002] Aromatic nitrile compounds are a very important class of synthons, and can undergo various functional group transformations. The benzonitrile structure widely exists in various natural products, and is the basic structural unit of many natural products, bioactive molecules and drug molecules, and these compounds have a variety of physiological activities and can be used as anti-androgen, anti-tumor drugs, anti-depressants Drugs, antipsychotics, tranquilizers, etc. (A.Kleemann, J.Engel, B.Kutscher and D.Reichert, Pharma-ceutical substances: syntheses, patents, applications, Georg Thieme Verlag, Stuttgart, New York, 4th ed, 2001 , pp.241-1599; Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem., 2003, 3513-3526; Smith, M. B.; March, J. March's Advanced Organi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C255/50C07C255/54C07C255/52C07C255/53C07C253/00C07C253/14
Inventor 戚朝荣胡晓寒江焕峰何海涛
Owner SOUTH CHINA UNIV OF TECH