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A synthetic method of 2-phenyl-3-cyano benzofuran compounds

A synthesis method and compound technology are applied in the field of cyanosynthesis of organic compounds, which can solve the problems of low selectivity and waste of metallic copper, and achieve the effects of easy availability of reaction raw materials, reduction of processes, and mild reaction conditions.

Inactive Publication Date: 2016-03-16
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 synthetic method of 2-phenyl-3-cyano benzofuran compounds
  • A synthetic method of 2-phenyl-3-cyano benzofuran compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0021] Example R 1 R 2 1 Ph 5-Me-Ph 2 4-Me-Ph 5-Me-Ph 3 4-OMe-Ph 5-Me-Ph 4 4-Cl-Ph 5-Me-Ph 5 4-F-Ph 5-Me-Ph 6 3-Cl-Ph 5-Me-Ph 7 1-Naphthyl 5-Me-Ph 8 2-thiophene 5-Me-Ph 9 Ph Ph 10 Ph 5-Cl-Ph

Embodiment 1

[0023] Add 5-methylsalicylaldehyde (0.5mmol), Cu(OAc) to the reaction flask in turn at room temperature (20-35°C) 2 (0.1mmol), phenylacetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stirred and heated to 100°C until the reaction of 5-methyl salicylaldehyde was complete. After the reaction, the reaction solution was cooled to room temperature, then added to 20ml of water, extracted three times with dichloromethane, using 10ml of dichloromethane each time, separated by silica gel chromatography column, and distilled under reduced pressure. The yield was 74%, and the identification result was: Whitesolid, mp112–113℃. 1 HNMR (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 CNMR (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: cacld.forC 16 h 11 NO[M + ], 233.0841; found: 233.0845.

Embodiment 2

[0025] Add 5-methylsalicylaldehyde (0.5mmol), Cu(OAc) to the reaction flask in turn at room temperature (20-35°C) 2 (0.1mmol), p-tolueneacetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stirred and heated to 100°C until the reaction of 5-methyl salicylaldehyde was complete. After the reaction, the reaction solution was cooled to room temperature, then added to 20ml of water, extracted three times with dichloromethane, using 10ml of dichloromethane each time, separated by silica gel chromatography column, and distilled under reduced pressure. The yield was 56%, and the identification result was: Whitesolid, mp136–137℃. 1 HNMR (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 CNMR (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: cacld.forC 17 h 13 NO[M + ], 247.0997; found: 247...

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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 class of important chemical intermediates, 2-phenyl-3-cyanobenzofuran compounds are widely used in pharmaceutical, pesticide, dyestuff and other industries. At present, various methods for synthesizing 2-phenyl-3-cyanobenzofuran compounds have been published. LeiWang (Org.Biomol.Chem., 2012, vol10, p7184–7196) et al reported the formation of intermediate alkenonitrile compounds from phenol and 3-phenylpropionitrile under the action of a base, and then under the catalysis of palladium acetate 2-Phenyl-3-cyanobenzofurans are formed. The intermediate alkene nitrile compound formed in this method has Z formula and E formula, and only E formula can obtain final product, and selectivity is not very good. KouichiOhe (Chem.Commun., 2012, vol48, p3127–3129) et al...

Claims

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Application Information

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Patent Type & Authority Applications(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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