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Method for synthesizing difluoromethyl compound

A technology of difluoromethyl and synthesis method, which is applied in the field of synthesis of fluorine-containing medicines and pesticide intermediates, can solve the problems of complex synthesis, limited application, high toxicity, etc., and achieve high universality, high yield, and mild conditions Effect

Active Publication Date: 2010-09-15
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Trifluoromethyl metal compounds such as Me 3 SnCF 3 、PhHgCF 3 , BrZnCF 3 , BrCdCF 3 It can also be used as a carbene reagent, but its synthesis is relatively complicated and its toxicity is high, which greatly limits its application ((a) Seyferth, D.; Hoppe, S.P., J.Organomet.Chem., 1971, 26, 64. (b) Seyferth, D.; Hoppe, S.P; Darragh. K.V., J. Am. Chem. Soc. 1969, 91, 6536.)

Method used

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  • Method for synthesizing difluoromethyl compound

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Embodiment 1

[0021] Under nitrogen protection, p-phenylphenol (85mg, 0.5mmol), 3 ml of DMF were added to the reaction tube, NaH (60%) (26mg, 0.65mmol) was added at 5°C, and after stirring for 10min, difluoromethyltributylammonium chloride (164mg, 0.6 mmol), let it rise to room temperature slowly, and stirred for 2 hours. Join H 2 O, extracted with ether, washed once with saturated brine, anhydrous MgSO 4 Dry the organic layer. Column chromatography (silica gel column, sherwood oil and ethyl acetate washing) obtains product 83 mg, yield 75%.

Embodiment 2

[0023] Under nitrogen protection, phenol (49mg, 0.5mmol), 3 ml of DMF were added to the reaction tube, NaH (60%) (26mg, 0.65mmol) was added at 5°C, and after stirring for 10min, difluoromethyltributylammonium chloride (164mg, 0.6 mmol), let it rise to room temperature slowly, and stirred for 2 hours. Join H 2 O, ether extraction. get product With trifluorotoluene as internal standard, the yield of NMR fluorine spectrum is 52%.

Embodiment 3

[0025] Under nitrogen protection, p-nitrophenol (70mg, 0.5mmol), 3 ml of DMF were added to the reaction tube, NaH (60%) (26mg, 0.65mmol) was added at 5°C, and after stirring for 10min, difluoromethyltributylammonium chloride (164mg, 0.6 mmol), let it rise to room temperature slowly, and stirred for 2 hours. Join H 2 O, extracted with ether, washed once with saturated brine, anhydrous MgSO 4 Dry the organic layer. Column chromatography (silica gel column, sherwood oil and ethyl acetate washing) obtains product 93 mg, yield 98%.

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Abstract

The invention relates to a method for synthesizing compound containing difluoromethyl group, in particular to a method for synthesizing difluoromethyl ether, thioether, selenide, difluoromethyl amine and difluoromethyl alkyne compounds. Difluoromethyl trialkyl ammonium salt (RaRbRc(CF2H)N+X-) applied as a difluorocarbene reagent and a compound containing active hydrogen are used as raw materials, and a compound in which the active hydrogen is substituted by difluoromethyl is obtained in the presence of alkali at proper temperature. The active hydrogen compound is a compound having active hydrogen on the hetero atom of oxygen, sulfur, selenium or ammonia or on the end of terminal alkyne. The difluoromethyl trialkyl ammonium salt used in the invention is a highly effective difluorocarbene reagent with a good universal adaptation.

Description

technical field [0001] The present invention relates to the synthetic method of fluorine-containing medicine, pesticide intermediate, is to utilize difluoromethyl trialkylammonium salt (R for the first time) a R b R c (CF 2 H) N + x - ) to synthesize a method containing difluoromethyl compounds. Background technique [0002] Due to the unique properties of fluorine atoms, a large number of facts show that the introduction of difluoromethyl groups into molecules can often effectively improve the physiological activity of organic molecules. Therefore, compounds containing difluoromethyl have been paid more and more attention in the fields of medicine, pesticides and 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. ) Using difluorocarbene as a difluoromethyl or difluoromethylene building block is a ...

Claims

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Application Information

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IPC IPC(8): C07B47/00C07C43/225C07C41/01C07C205/37C07C201/12C07C323/03C07C323/09C07C319/14C07D257/04C07D235/04C07D249/18C07D231/08C07D235/18C07D233/56C07C391/02C07C22/08C07C17/263
Inventor 胡金波王飞黄维洲
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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