New trifluoro methylation reagent and preparation and application thereof

A technology of trifluoromethylation and trifluoromethyl metal, applied in the direction of introducing hydroxyl and halogen preparation, sulfonic acid preparation, halogenated hydrocarbon preparation, etc., can solve the problems of difficult preparation, high equipment requirements, long process route, etc.

Active Publication Date: 2014-09-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw materials of the preparation method of the above reagents are relatively expensive, the process route is long, the equipment requirements are high, it is difficult to prepare, and it is also difficult to apply to the reaction
[0005] In summary, there is still a lack of a trifluoromethylation reagent with simple preparation process, mild reaction conditions and low cost in this area.

Method used

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  • New trifluoro methylation reagent and preparation and application thereof
  • New trifluoro methylation reagent and preparation and application thereof
  • New trifluoro methylation reagent and preparation and application thereof

Examples

Experimental program
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preparation example Construction

[0132] The raw materials of the preparation method are readily available, and the compound of the formula II can be prepared by any prior art or obtained through commercial channels. Preferably, the compound of the formula II can use common fluorine chemical raw materials.

[0133] The method has a very high yield, generally ≥80%, and in another preferred embodiment, the yield of the reaction is ≥90%.

[0134] In a preferred embodiment of the present invention, described method comprises the following steps:

[0135] 1) Add the compound of formula III into the reactor, add an inert solvent and mix well;

[0136] 2) Add the compound of formula II dropwise into the reaction system;

[0137] 3) Stir overnight at -20-50°C;

[0138] 4) Filtrate and collect the filtrate, spin the solvent to obtain the compound of formula I;

[0139] In the above formulas, the definitions of each group are as described above.

[0140] The fluorosulfone difluoroacetic acid metal salt in acetonitri...

Embodiment 1

[0168] Embodiment 1 Fluorosulfone base silver difluoroacetate ((FSO 2 CF 2 COO) 2 Ag) Preparation

[0169] In a 500ml three-necked bottle equipped with electromagnetic stirring, constant pressure dropping funnel and reflux condenser, add silver carbonate Ag 2 CO 3 (100g, 0.363mol) and ether (200ml), add fluorosulfone difluoroacetic acid (FSO 2 CF 2 COOH, 129g, 0.725mol), stirred overnight. After filtration, wash the filter residue three times with a little ether, combine the ether layers, and remove the ether under reduced pressure to obtain white solid fluorosulfone silver difluoroacetate (FSO 2 CF 2 COOAg), yield 90%.

[0170] 19 F NMR (CDCl 3 ):40ppm(1F),-103ppm(2F)

[0171] The white solid (FSO 2 CF 2 COOAg) was recrystallized in toluene, and the obtained crystal structure was as attached figure 1 shown.

Embodiment 2

[0172] Embodiment 2 fluorosulfone base copper difluoroacetate ((FSO 2 CF 2 COO) 2 Cu) Preparation

[0173] In a 500ml three-necked bottle equipped with electromagnetic stirring, constant pressure dropping funnel and reflux condenser, add basic copper carbonate Cu 2 (OH) 2 CO 3 (50g, 0.226mol) and ether (200ml), add fluorosulfone difluoroacetic acid (FSO 2 CF 2 COOH, 160g, 0.904mol), stirred overnight. After filtering, wash the filter residue three times with a little ether, combine the ether layers, and remove the ether under reduced pressure to obtain a blue-green solid fluorosulfone group copper difluoroacetate ((FSO 2 CF 2 COO) 2 Cu), yield 95%. The crystal structure of the product is attached figure 2 shown.

[0174] 19 F NMR (CDCl 3 ): 40ppm (1F), -103ppm (2F).

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Abstract

The invention relates to a new trifluoro methylation reagent and preparation and application thereof, and in particular relates to a compound with a structure shown as a formula I, a preparing method thereof and application thereof as a trifluoro methylation reagent. In the formula, the definition of each group is as defined in the specification. The starting materials of the new trifluoro methylation reagent are cheap and easy to obtain, the reaction condition is mild, the post treatment is simple, the product can be used as a variety of potential trifluoro methylation reagents, the yield is high, the equipment requirement is low, and the new trifluoro methylation reagent has wide prospects of industrial application. (FSO2CF2COO) zM I.

Description

technical field [0001] The invention belongs to the field of organic fluorine chemistry, in particular, the invention relates to a novel trifluoromethylation reagent and its preparation and application. Background technique [0002] The introduction of fluorine atoms into the compound can greatly change the biological activity and physical properties of the compound, leading to the production of a series of drugs and new materials. Therefore, the field of compound synthesis needs to find a method for efficiently introducing fluorine atoms into compound molecules. [0003] Trifluoromethyl metal species is a relatively unstable species, but it can be trifluoromethylated with aldehydes, ketones, alkenes, alkynes, aromatics, heterocyclic compounds and their halides to synthesize three A series of fluoromethyl compounds are widely used in medicine, pesticide, material and fine chemical industry, or directly used as medicine, pesticide, material and fine chemical, or synthetic me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/84C07C303/22C07B39/00C07C22/08C07C22/00C07C17/32C07C33/46C07C29/64C07J1/00
Inventor 陈庆云赵刚刘超郭勇肖吉昌赵帅王文贵姜东方
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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