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Method for producing trifluoromethyl thioalkyl compound

A kind of technology of trifluoromethyl thioalkyl group and production method, applied in directions such as thioether preparation, organic chemistry and the like

Active Publication Date: 2017-08-18
KUMIAI CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, only highly reactive halogenated aryl compounds are used as raw materials in the production method described in Non-Patent Document 1

Method used

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  • Method for producing trifluoromethyl thioalkyl compound
  • Method for producing trifluoromethyl thioalkyl compound
  • Method for producing trifluoromethyl thioalkyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0184] Production of 6-(trifluoromethylthio)hexyl acetate

[0185] [chemical 5]

[0186]

[0187] Add 7.2 mL (94 mmol) of thiophosgene dropwise to 400 mL of acetonitrile containing 15.0 g (67.2 mmol) of 6-bromohexyl acetate and 23.4 g (403 mmol) of potassium fluoride over a period of 1 hour using a dropping funnel solution (the temperature in the reaction system at this time was 80° C.). After stirring the reaction mixture under reflux for 1 hour, the reaction mixture was naturally cooled to room temperature, and the insoluble matter was filtered off. Water was added to the filtrate, followed by extraction with diisopropyl ether, and the organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine. The organic layer obtained by liquid separation was dried over anhydrous magnesium sulfate, and inorganic substances were filtered off, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by vacuum distill...

Embodiment 2～4

[0191] Change the addition temperature and addition time respectively, dropwise add thiophosgene 0.60mL (7.7mmol) acetonitrile 4.5mL solution to 6-bromohexyl acetate 1.2g (5.5mmol), potassium fluoride 1.9g (33mmol) acetonitrile 32mL solution. After stirring for 1 hour, a part of the reaction mixture was analyzed by GC, and the yield of the target product was calculated by the area percentage method. The results are summarized in Table 1 in the same manner as in Example 1. In addition, in the GC analysis of Examples 2-4, the unreacted raw material compound (6-bromohexyl acetate) was detected other than the object.

[0192] [Table 1]

[0193]

Embodiment 5

[0195] Production of ethyl 6-(trifluoromethylthio)hexanoate

[0196] [chemical 6]

[0197]

[0198] Add 1.2 mL (15 mmol) of thiophosgene in 3.8 mL of acetonitrile dropwise to 62 mL of acetonitrile containing 2.4 g (11 mmol) of ethyl 6-bromohexanoate and 3.8 g (65 mmol) of potassium fluoride over 1 hour under heating to reflux solution (the temperature in the reaction system at this time was 80° C.). The reaction mixture was stirred under reflux for 1 hour, and then cooled to room temperature naturally. Water was added to the reaction mixture, followed by extraction with diisopropyl ether, and the organic layer was washed with saturated aqueous sodium bicarbonate and saturated brine. After the organic layer obtained by liquid separation was dried over anhydrous magnesium sulfate, the inorganic matter was filtered off, and the solvent was distilled off under reduced pressure to obtain 2.5 g of ethyl 6-(trifluoromethylthio)hexanoate as a reddish-brown liquid ( Yield 96%). ...

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Abstract

A method for producing a trifluoromethyl thioalkyl compound represented by general formula (1) (wherein R represents a C1-C10 alkyl group which may be substituted by R1, or the like; R1 represents a C1-C4 alkyl group or the like; and R2 represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group or the like), which is characterized by adding thiophosgene at an addition temperature of 45 DEG C or more for an addition time of 0.25 hour or more in the presence of a compound represented by general formula (2) (wherein R is as defined in general formula (1); and L represents a halogen atom, a C1-C4 alkylsulfonyloxy group or the like) and a fluorine compound.

Description

technical field [0001] The present invention relates to a method for producing a trifluoromethylthioalkyl compound, and particularly to a method for producing a trifluoromethylthioalkyl compound using a low-reactivity alkyl compound as a raw material. Background technique [0002] Fluoroalkylthio groups are useful substituents in pharmaceutical and pesticide compounds. For example, the pest control agent disclosed in Patent Document 1 has a trifluoroethylsulfinyl group on the benzene ring and a trifluoromethylthio group at the end of the alkoxy side chain, and the fluoroalkylthio group has a significant role in pest control activity. play an important role in the expression. [0003] In the method for producing a trifluoromethylthio group at the end of an alkoxy side chain described in Patent Document 1, first, a halogenated alkyl compound as a raw material is reacted with a metal thiocyanate to synthesize a thiocyanate compound ( "Manufacturing Method 11" of Patent Docume...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/03C07C323/12C07C323/20C07C323/52
CPCC07C319/14C07C323/03C07C323/12C07C323/20C07C323/52
Inventor 金原明
Owner KUMIAI CHEM IND CO LTD
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