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Method for preparing alkyl sulfonyl fluoride

A technology of alkylsulfonyl and alkyl groups, applied in the field of preparing alkylsulfonyl fluoride, can solve the problem of few synthesis methods, and achieve the effect of simple synthesis method and high yield

Active Publication Date: 2021-11-26
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For alkylsulfonyl fluoride, the current synthesis methods are less and limited to alkyl halides, ESF building blocks

Method used

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  • Method for preparing alkyl sulfonyl fluoride
  • Method for preparing alkyl sulfonyl fluoride
  • Method for preparing alkyl sulfonyl fluoride

Examples

Experimental program
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Effect test

preparation example Construction

[0052] The method of preparing reduction activated esters of the alkyl carboxylic acid of the present invention comprises the steps of:

[0053]

[0054] Taking R as a cyclohexyl group, 1.28 g (10 mmol) of cyclohexylhalic acid, 1.63 g (10 mmol) N-hydroxyphthalimide, 0.12 g (1 mmol) DMAP, add 100 ml of two Chloromethane is solvent and stirred vigorously. Then 1.7 ml (10 mmol) DIC was added, and the mixture was stirred at room temperature for 3-5 hours. The mixture was filtered through diatomite or silica gel, and then flushed with dichloromethane. The filtrate was collected and the solvent was removed under reduced pressure. Purification by column chromatography or purification method to give the desired carboxylic acid reducing active ester raw material.

[0055] All carboxylic acid resection active esters of the present invention are prepared according to this method.

Embodiment 1

[0057] Cyclohexylsulfonyl fluoride synthesis, reducing active ester of cyclohexylcarboxylic acid as a template substrate, NA 2 S 2 O 4 As the sulfur dioxide source, NFSI is a fluorine source, a solvent is DMF, and a sulfonyl fluoride is formed under an inert gas protection and heating. The reactive and specific implementation are as follows:

[0058]

[0059] Take 10ml of the tube into the magnet, weigh 54.9 mg (0.2 mmol) reductive active ester of cyclohexylcycarboxylic acid, 52.3 mg (0.3 mmol) NA 2 S 2 O 4 The addition of the argon was added three times, and N, N-dimethylformamide (DMF) 2 ml was added to 80 ° C for 9 hours under argon. 0.6 mmol) NFSI reaction for 4 hours. After completion of the reaction, 4-methoxy trifluoromethoxybenzene was added as the internal standard, and the nuclear magnetic analysis was 0%.

Embodiment 2

[0061] Cyclohexylsulfonyl fluoride synthesis, reducing active ester of cyclohexylcarboxylic acid as a template substrate, NA 2 S 2 O 4 As the sulfur dioxide source, NFSI is fluorine source, solvent is DMF, water as an additive, and the reaction is formed into sulfonyl fluoride. The reaction is as follows:

[0062]

[0063] Take 10ml of the tube into the magnet, weigh 54.9 mg (0.2 mmol) reductive active ester of cyclohexylcycarboxylic acid, 52.3 mg (0.3 mmol) NA 2 S 2 O 4 Add it, the argon is placed three times, with N, N-dimethylformamide (DMF) and water under argon (V DMF : V 水 = 2: 0.4, mL) was used as a solvent and additive, and the mixture was heated to 80 ° C for 9 hours, cooled to room temperature, and the reaction was reacted for 4 hours. After completion of the reaction, 4-methoxy trifluoromethoxybenzene was added as the internal standard, and the nuclear magnetic analysis was added to the flu fluoroscopy rate of 22%.

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Abstract

The invention relates to a method for preparing alkyl sulfuryl fluoride, which comprises the following step: by taking reduced active ester converted from alkyl carboxylic acid as a raw material, a sulfur dioxide substitute reagent as a sulfur dioxide source and an electrophilic fluorinating reagent as a fluorine source, reacting under the conditions of reducing metal reduction and inert gas protection to obtain the target product alkyl sulfuryl fluoride. Compared with the prior art, the synthesis method disclosed by the invention is simple, has selectivity of in-situ introduction of sulfonyl fluoride groups and relatively high yield, and is easy to realize large-scale production.

Description

Technical field [0001] The present invention relates to the field of synthetic chemical techniques, and more particularly to a method of preparing an alkylsulfonyl fluoride. Background technique [0002] Fluorosulfonyl (SO 2 F) is a unique fluorine-containing sulfur-containing functional group, since the fluorine atom has superior suction electronics, it is difficult to disconnect the S-F key by splitting. In particular, it is in the proton (h when the nucleophilic reactive reaction occurs. + ) Or silicon ions (R 3 Si + ) The fluoride ions that can be stabilized, so that such reactions have the advantages of high driving force, not afraid of water, specificity and controllability. In addition to this, compared with other S (VI) -X keys, it also has hydrolyzable stability, anti-reducing property, and chemical selection reactivity in the center of sulfur. Because of this, the sulfonyl fluoride is widely used in the field of chemical, surface chemistry, biochemical and organic synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/85C07C303/02C07C309/80C07C309/81C07C309/82
CPCC07C303/02C07D209/48C07C2601/14C07C2603/74C07C309/85C07C309/80C07C309/81C07C309/82
Inventor 刘超马占虎马晓玉胡晓钧庞婉吴晶晶
Owner SHANGHAI INST OF TECH
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