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Method of synthesizing compound containing difluoromethyl group

A technology of difluoro-halomethyl phenyl ketones and compounds, which is applied in the field of synthesizing compounds containing difluoromethyl groups, can solve the problems of destroying the ozone layer, and achieve the effect of mild reaction conditions and high yield

Inactive Publication Date: 2007-03-07
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

Their shortcoming is that Freon gas can destroy the ozone layer, and ClF2CCOONa and ClF2CCOOMe are directly or indirectly passed through the gas that can destroy the ozone layer ((a) Christensen, S.B., IV; Dabbs, H.E.; Karpinski, J.M.PCT International Application, WO 96 / 23754, 1996.(b) Ho, J.Z.; Elmore, C.S.; Wallace, M.A.; Yao, D.; Braun, M.P.; 88, 1040. (c) O'shea, P.D.; Chen, C.-Y.; Chen, W.; Dagneau, P.; Frey, L.F.; Grabowski, E.J.J.; .; Tillyer, R.D.; Roy, A.; Wang, X.; Zhao, D.J.Org.Chem.2005, 70, 3021.)

Method used

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  • Method of synthesizing compound containing difluoromethyl group
  • Method of synthesizing compound containing difluoromethyl group
  • Method of synthesizing compound containing difluoromethyl group

Examples

Experimental program
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Embodiment 1

[0017] At an oil bath temperature of 50°C, put 0.33 g of 1,3,5-tribromophenol, 5 ml of acetonitrile, 2 ml of 30% KOH aqueous solution, and 0.452 g of difluorochloromethylphenyl sulfone into a sealed tube The reaction was stirred for 4 hours. After the reaction was completed, it was cooled to room temperature, and ethyl acetate and water were added for extraction. The obtained organic phase was washed with saturated brine, then dried by adding anhydrous magnesium sulfate, and the solvent was spin-dried, and 0.32 g of the product 1,3,5-tribromophenyl difluoromethyl ether was separated by silica gel chromatography, 84 %Yield. The reaction formula is as follows:

[0018]

Embodiment 2

[0020] At an oil bath temperature of 80°C, put 0.33 g of 1,3,5-tribromophenol, 5 ml of acetonitrile, 3 ml of 30% KOH aqueous solution, and 0.950 g of difluorochloromethyl phenyl ketone into a sealed tube The reaction was stirred for 4 hours. After the reaction was completed, it was cooled to room temperature, and ethyl acetate and water were added for extraction. The obtained organic phase was washed with saturated brine, then dried by adding anhydrous magnesium sulfate, and the solvent was spin-dried, and the product 1,3,5-tribromophenyl difluoromethyl ether was separated by silica gel chromatography. 0.185 g, 50 %Yield. The reaction formula is as follows:

[0021]

Embodiment 3

[0023] At an oil bath temperature of 50°C, 0.196 g of p-vinylphenylphenol 5 ml of acetonitrile, 2 ml of 30% KOH aqueous solution, and 0.452 g of difluorochloromethylphenyl sulfone were placed in a sealed tube and stirred for 4 hours. get the product 0.199 g, 81% yield.

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Abstract

The invention discloses a synthesizing method of methyl difluoride ether and amine, which is characterized by the following: neutralizing soluble organic solvent at 50-80 deg.c; reacting compound with monohydric hydrogen or nitrogen atom on the hydrogen and univalent metal hydroxide compound solution and difluo-monochloromethyl phenylketonuria or difluo-monochloromethyl phenylsulfone for 1-5h to produce the product with hydrogen replaced by fluorine methyl.

Description

technical field [0001] The present invention relates to a method for synthesizing intermediates of fluorine-containing medicines and pesticides, which is a method for synthesizing compounds containing difluoromethyl groups, specifically for synthesizing difluoromethyl aryl ether and difluoromethyl amine method, an efficient and environmentally friendly method for the synthesis of difluoromethoxyaryl compounds. Background technique [0002] Difluoromethoxy group can significantly enhance the physiological activity of organic molecular compounds than trifluoromethoxy group, and plays an important role in many bioorganic molecules and liquid crystal materials ((a) Kirsch, P.Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004. (b) Organofluorine Compounds: chemistry and Applications; Hiyama, T., Ed.; Springer: New York, 2000. (c) Kirsch, P.; Bremer, B. Angew. Chem . Int. Ed. 2000, 39, 4216.). Although aliphatic chain compounds contain...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C43/215C07C43/20C07D215/26C07D233/58C07B39/00
Inventor 胡金波郑吉张来俊
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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