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Reagent and method for preparing a fluorinated and silylated derivative

A technology of silylation and derivatives, which is applied in the field of synthesis of silylation derivatives, and can solve problems such as impossibility of industrial application, excessive cost, and high cost

Inactive Publication Date: 2011-09-21
RHODIA CHEM SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] These silylated derivatives are particularly difficult to obtain and require costly operating procedures, making their industrial application nearly impossible, or prohibitively expensive

Method used

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  • Reagent and method for preparing a fluorinated and silylated derivative
  • Reagent and method for preparing a fluorinated and silylated derivative
  • Reagent and method for preparing a fluorinated and silylated derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0112] Embodiment 1: Utilize various alkalis to carry out qualitative test

[0113] A series of experiments were carried out using various bases.

[0114] The base (1 mmol) was charged into a 60 ml Schott tube under argon atmosphere. DMF (2ml) was added at 20°C under an argon atmosphere, followed by trimethylsilyl trifluoroacetate (372mg, 2mmol).

[0115] The tube was closed and the reaction mixture was heated at 140 °C for the desired time.

[0116] After returning to 20° C., the reaction medium was analyzed without further processing.

[0117] The properties are summarized in the table below.

[0118] Table (I)

[0119]

[0120] *:ordinary

[0121] **:medium

[0122] ***:good

[0123] ****:very good

[0124] *****: Excellent

Embodiment II

[0125] Example II: Trimethylsilyl trifluoroacetate in the presence of potassium trifluoroacetate

[0126] Potassium trifluoroacetate (152 mg, 1 mmol) was charged to a 60 ml Schott tube under argon atmosphere.

[0127] DMF (2ml) was added at 20°C under an argon atmosphere, followed by trimethylsilyl trifluoroacetate (372mg, 2mmol).

[0128] The tube was closed and the reaction mixture was heated at 140 °C for the desired time.

[0129] After returning to 20° C., the reaction medium was analyzed without further processing.

[0130] The properties are summarized in the table below.

[0131] Table (II)

[0132] test

[0133] (a) by using the internal standard 19 F NMR measurement (b) RY=8% relative to TMSTFA, RY=75% relative to KTFA.

Embodiment III

[0134] Example III: Trimethylsilyl trifluoroacetate in the presence of potassium chloride

[0135] Potassium chloride (74.5 mg, 1 mmol) was charged to a 60 ml Schott tube under argon atmosphere.

[0136] DMF (2ml) was added at 20°C under an argon atmosphere, followed by trimethylsilyl trifluoroacetate (372mg, 2mmol).

[0137] The tube was closed and the reaction mixture was heated at 140 °C for the desired time.

[0138] After returning to 20° C., the reaction medium was analyzed without further processing.

[0139] The properties are summarized in the table below.

[0140] Table (III)

[0141] test

[0142] (a) by using the internal standard 19 F NMR determination (b) source of chloride: Me 4 NCl.

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Abstract

The invention relates to a method for preparing a fluorinated and silylated derivative having a bond between the bearing carbon of at least one fluorine and one silicon. This method comprises at least one step during which a derivative of formula (I) Rf-CO-O-D, in which D is selected among silylated radicals, is placed in the presence of a base. The inventive method is used for synthesizing fluorinated derivatives.

Description

field of invention [0001] The subject of the present invention is a process for the production of fluorinated and silylated derivatives having a bond between carbon bearing at least one fluorine and silicon. [0002] The invention relates more particularly to the synthesis of silylated derivatives in which one of the silicon-bonded carbons carries one, advantageously two, or even three fluorine atoms. Background technique [0003] Fluoroalkylated derivatives, especially perfluoroalkylated derivatives, have been developed in the fields of pharmaceuticals and agrochemicals. These compounds are particularly difficult and expensive to prepare, except in some specific cases. [0004] One of the ways to perform perfluoroalkylation is to use Rf - Carbanions or use compounds that react like carbanions. [0005] Among the derivatives that react like carbanions, mention may be made of Rf-Si(Me) 3 type of reagent. where Rf is CF 3 In the case of , it is called "Ruppert's reagent"...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C07F7/08
CPCC07F7/1896Y02P20/582
Inventor T·维达尔N·罗克L·圣-雅尔姆
Owner RHODIA CHEM SA
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