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A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene

A technology of trifluoromethylthiobenzene and fluoromethylthiobenzene, which is applied in the field of trifluoromethylthiobenzene compounds and their synthesis, can solve problems such as limiting practical applications, and achieve low production costs, safe reaction conditions, and efficient reaction The effect of mild conditions

Active Publication Date: 2019-11-22
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently the Wangelin group reported the use of 1,2-bis(trifluoromethyl)disulfane (F 3 CS) 2 . Visible-light-catalyzed trifluorothiolation of diazonium salts, however, (F 3 CS) 2 .is a low boiling point (bp≈34°C) and toxic reagent, which limits its practical application

Method used

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  • A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene
  • A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene
  • A process for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene

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Embodiment 1

[0047] The trifluoromethylthiobenzene compound prepared in this embodiment is a 4-methoxytrifluoromethylthiobenzene compound, and its synthesis method comprises the following steps:

[0048] Under white light irradiation, 4-methoxybenzenediazonium tetrafluoroborate (aryl diazonium salt), tris(2,2'-biphenylpyridine)ruthenium bis(hexafluorophosphate) and S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate were uniformly mixed in thionyl chloride, and reacted at room temperature 20-25°C after mixing, and detected by spot plate (petroleum ether: ethyl acetate Ester=50:1, volume ratio, the same below) The time to determine the end of the reaction is 12 hours, add water to extract after the end of the reaction, separate to obtain the liquid organic phase, get 4g of anhydrous Na 2 SO 4Dry the liquid organic phase, import the dried liquid organic phase into a 250ml flask, remove the solvent under vacuum with a rotary evaporator (i.e. concentrate), carry out column chromatography and q...

Embodiment 2

[0055] The trifluoromethylthiobenzene compound prepared in this embodiment is a 4-phenoxytrifluoromethylthiobenzene compound, and its synthesis method comprises the following steps:

[0056] Under white light irradiation, 4-phenoxybenzenediazonium tetrafluoroborate (aryl diazonium salt), tris(2,2'-biphenylpyridine) ruthenium bis(hexafluorophosphate) salt Mix evenly with S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate in thionyl chloride, react at room temperature 20-25°C after mixing, and determine the reaction by spot plate detection (petroleum ether) The time of finishing is 11 hours, and water is added to extract again after reaction finishes, and separation obtains liquid organic phase, gets 4g anhydrous Na 2 SO 4 Dry the liquid organic phase, import the dried liquid organic phase into a 250ml flask, evaporate and concentrate in a rotary evaporator, and perform column chromatography for quick separation to obtain 4-phenoxytrifluoromethylthiobenzene as a white solid, wh...

Embodiment 3

[0063] The trifluoromethylthiobenzene compound prepared in this embodiment is 4-methylthiotrifluoromethylthiobenzene compound, and its synthesis method comprises the following steps:

[0064] Under white light irradiation, 4-methylthiobenzenediazonium tetrafluoroborate (aryl diazonium salt), tris(2,2′-biphenylpyridine) ruthenium bis(hexafluorophosphate) Mix evenly with S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate in thionyl chloride, react at room temperature 20-25°C after mixing, and determine the reaction by spot plate detection (petroleum ether) The time of finishing is 12 hours, adds water again after reaction finishes and extracts, separates and obtains liquid organic phase, gets 4g anhydrous Na 2 SO 4 Dry the liquid organic phase, introduce the dried liquid organic phase into a 250ml flask, evaporate and concentrate in a rotary evaporator (rotary evaporator), and perform column chromatography for rapid separation to obtain yellow oily 4-methylthiotrifluoromethylsu...

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Abstract

The invention discloses a synthetic method of [(trifluoromethyl)thio]benzene compounds, particularly a method for converting substituted phenyl diazonium salts into [(trifluoromethyl)thio]benzene. Themethod comprises the following steps: under white light irradiation, adding an aryl diazonium salt, tris(2,2'-bipyridine)ruthenium(II) hexafluorophosphate and S-trifluoromethyl-4-methoxybenzenesulfonyl sulfate into a solvent and uniformly mixing the mixture; after mixing, reacting the mixture at the room temperature of 20-25 DEG C; determining the reaction ending time through spotting detection;after the reaction is finished, adding water for extraction; performing separation to obtain a liquid organic phase; drying the liquid organic phase with anhydrous Na2SO4; then removing a solvent; andperforming rapid separation with column chromatography to obtain a [(trifluoromethyl)thio]benzene compound. The method is mild in reaction condition, free of high-temperature and high-pressure reaction, safe in reaction condition and suitable for large-scale production and development.

Description

[0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a trifluoromethylthiobenzene compound and a synthesis method thereof. Background technique [0002] Trifluoromethylthio (SCF 3 ) has been highly valued by academia and industry because of its unique physical and chemical properties, and its good lipophilicity helps to adjust cell membrane permeability to improve bioavailability. [0003] Arylamines are widely used in laboratory research and industrial production because of their easy availability, low cost and diverse reactivity. Aromatic diazonium salts are easily prepared from aromatic amines and are important intermediates in organic transformations. In those Sandmeyer-type reactions, for the direct conversion of aromatic amino groups to boryl, phosphoryl, stannyl, and trifluoromethyl groups. Recently the Wangelin group reported the use of 1,2-bis(trifluoromethyl)disulfane (F 3 CS) 2 . Visible-light-catalyzed trifluorot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/20C07C323/03C07C323/62C07C323/09C07C323/22C07C319/14
CPCC07C323/03C07C323/09C07C323/20C07C323/22C07C323/62
Inventor 赵霞佟一凡郑先才芦逵
Owner TIANJIN NORMAL UNIVERSITY
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