A kind of synthetic method of 2-phenyl-3-cyanobenzofuran compound

A synthesis method and compound technology, which are applied in the field of organic compound cyanation synthesis, can solve the problems of waste of metallic copper, low selectivity and the like, and achieve the effects of reducing processes, readily available reaction raw materials and low production cost.

Inactive Publication Date: 2018-02-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Use 2.2 equivalents of cuprous cyanide as catalyst and cyanide source in the method, causing a large amount of waste of metal copper
Moreover, the reaction conditions require an oxygen environment, and the product is also a mixture of 2-phenyl-3-cyanobenzofuran compounds and 2-phenylbenzofuran compounds, and the selectivity is not high.

Method used

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  • A kind of synthetic method of 2-phenyl-3-cyanobenzofuran compound
  • A kind of synthetic method of 2-phenyl-3-cyanobenzofuran compound
  • A kind of synthetic method of 2-phenyl-3-cyanobenzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0021] Example

Embodiment 1

[0023] Add 5-methyl salicylaldehyde (0.5mmol), Cu(OAc) to the reaction flask at room temperature (20-35℃) 2 (0.1mmol), benzylacetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stir and heat to 100°C to react until the 5-methylsalicylic aldehyde reaction is complete. After the reaction, the reaction solution was cooled to room temperature, then added to 20ml of water, and extracted with dichloromethane three times, using 10ml of dichloromethane each time, separated by silica gel chromatography, and distilled under reduced pressure. The yield was 74%. The identification result was: White solid, mp 112–113°C. 1 H NMR(400MHz, CDCl 3 ): δ8.16(d,J=7.6Hz,2H), 7.57–7.46(m,4H), 7.43(d,J=8.4Hz,1H), 7.20(d,J=8.4Hz,1H), 2.47 (s,3H). 13 C NMR(100MHz, CDCl 3 ): δ161.6, 151.7, 134.5, 131.0, 129.1, 127.9, 127.7, 127.3, 126.4, 119.62, 114.5, 111.2, 87.7, 21.32. HRMS: Theoretical calculation value C 16 H 11 NO[M + ],233.0841; Test data: 233.0845.

Embodiment 2

[0025] Add 5-methyl salicylaldehyde (0.5mmol), Cu(OAc) to the reaction flask at room temperature (20-35℃) 2 (0.1mmol), p-toluene acetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stir and heat to 100°C to react until the 5-methylsalicylic aldehyde reaction is complete. After the reaction, the reaction solution was cooled to room temperature, and then added to 20ml of water, extracted with dichloromethane three times, using 10ml of dichloromethane each time, separated by silica gel chromatographic column, and distilled under reduced pressure. The yield was 56%. The identification result was: White solid, mp 136–137°C. 1 H NMR(400MHz, CDCl 3 ): δ8.06(d,J=8.4Hz,2H),7.48–7.45(m,1H),7.42(d,J=8.8Hz,1H),7.33(d,J=8.0Hz,2H),7.19 (dd,J=8.4,1.2Hz,1H),2.48(s,3H),2.43(s,3H). 13 C NMR(100MHz, CDCl 3 ): δ162.0, 151.6, 141.6, 134.4, 129.8, 127.4, 126.4, 125.2, 119.5, 114.7, 111.1, 87.0, 21.6, 21.3. HRMS: theoretical calculation value C 17 H 13 NO[M + ],247.0997; Test data: ...

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Abstract

A synthetic method of 2-phenyl-3-cyano benzofuran compounds is disclosed. The method includes weighing an aldehyde compound, an aryl acetonitrile compound, a catalyst and an alkali, according to a mole ratio of 1:1-2:0.2:4, adding into a reaction container, adding a solvent into the container until the aldehyde compound and the aryl acetonitrile compound are fully dissolved, putting the reaction container into an oil bath having temperature of 100-120 DEG C, reacting under stirring for 18-24 h, cooling to room temperature, adding water the volume of which is same as the volume of the solvent, extracting with dichloromethane for 2-4 times, separating by a silica column and distilling under vacuum to obtain a product that is one of the 2-phenyl-3-cyano benzofuran compounds. The method adopts a one-pot manner to produce the 2-phenyl-3-cyano benzofuran compounds, reduces processes of separation and purification of intermediates, and is simple in operation method, mild in reaction conditions, simple and easily available in raw materials, low in production cost, suitable for small-scale preparation in a laboratory and suitable for large-scale industrial production.

Description

Technical field [0001] The invention relates to a method for synthesizing organic compounds by cyanation, in particular to a method for synthesizing 2-phenyl-3-cyanobenzofuran compounds. Background technique [0002] As a kind of important chemical intermediates, 2-phenyl-3-cyanobenzofuran compounds are widely used in medicine, pesticide, dye and other industries. At present, many methods for synthesizing 2-phenyl-3-cyanobenzofurans have been published. Lei Wang (Org.Biomol.Chem., 2012, vol 10, p7184–7196) et al. reported that phenol and 3-phenylpropiolonitrile under the action of a base form an intermediate enenitrile compound, and then in the reaction of palladium acetate Under catalysis, 2-phenyl-3-cyanobenzofuran compounds are formed. The intermediate alkene nitrile compounds formed in the method have the Z formula and the E formula, and only the E formula can obtain the final product, and the selectivity is not very good. Kouichi Ohe (Chem. Commun., 2012, vol 48, p3127–31...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/84
CPCC07D307/84
Inventor 吕萍王彦广张莲鹏温俏冬
Owner ZHEJIANG UNIV
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