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Synthetic method of aryl trifluoromethylthio compound

An aryl trifluoromethylthio group and a synthesis method technology are applied in the field of organic compound synthesis to achieve the effects of simple and safe operation, mild conditions and wide substrate applicability

Active Publication Date: 2020-06-05
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Aiming at the shortcomings of the existing synthetic routes, the present invention provides a synthetic method for aryl trifluoromethylthio compounds, which has the advantages of simple process and convenient operation.

Method used

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  • Synthetic method of aryl trifluoromethylthio compound
  • Synthetic method of aryl trifluoromethylthio compound
  • Synthetic method of aryl trifluoromethylthio compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] Add 4-methoxythiophenol (0.3mmol), sodium trifluoromethanesulfinate (0.9mmol), tetrabutylammonium tetrafluoroborate (0.3mmol) to a 25mL undivided electrolytic cell equipped with a magnetic stirrer. ), sodium bromide (0.6mmol), and then add 8.0mL acetonitrile; fix the reaction tube on a magnetic stirrer, add electrodes (graphite cathode, graphite anode) through 20mA constant current electrolysis, while uniformly stirring the reaction solution; the mixture is at room temperature After 8 hours of reaction at 25°C, the reaction is complete; add appropriate amount of water to the reaction solution, extract with ethyl acetate, dry with anhydrous sodium sulfate, and finally use a rotary evaporator to remove the solvent. The crude product is subjected to column chromatography (petroleum ether). : Ethyl acetate=30:1) The target product (3a) was obtained by separation and purification with a yield of 76%. The NMR data of this compound are: 1 HNMR(400MHz, CDCl 3 )δ7.57(d,J...

Embodiment 2

[0032]

[0033] Use 4-bromothiophenol (1b) instead of 4-methoxythiophenol (1a), and the others are the same as in Example 1. Column chromatography (petroleum ether) gave the target product (3b) with a yield of 60%. The NMR data of this compound are: 1 HNMR(600MHz, CDCl 3 )δ7.57-7.54(m,2H),7.52-7.49(m,2H). 13 C NMR(151MHz, CDCl 3 )δ137.81,132.87,131.46(q,J=309.55Hz),126.07,123.49(d,J=2.3Hz). 19 F NMR(565MHz, CDCl 3 )δ-42.64(s,3F).

Embodiment 3

[0035]

[0036] Use 4-acetylthiophenol (1c) instead of 4-methoxythiophenol (1a), and the others are the same as in Example 1. Column chromatography (dichloromethane) gave the target product (3c) with a yield of 66%. The NMR data of this compound are: 1 H NMR(600MHz, DMSO-d 6 )δ10.22(s,1H), 7.70--7.67(m,2H), 7.61--7.58(m,2H), 2.03(s,3H). 13 C NMR(151MHz, DMSO-d 6 )δ169.46,142.82,137.80,130.14(q,J=308.1Hz), 120.32,116.05(d,J=2.3Hz), 24.63. 19 FNMR(565MHz,DMSO-d 6 )δ-42.79(s, 3F).

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Abstract

The invention discloses a synthesis method of an aryl trifluoromethylthio compound. Aryl thiophenol and sodium trifluoromethanesulfinate are adopted as raw materials, constant-current electrolysis isperformed in the presence of a supporting electrolyte to implement coupling of carbon-sulfur bonds, and separation and purification are performed to obtain the aryl trifluoromethylthio compound. According to the method, an electrochemical synthesis method is applied, the aryl trifluoromethylthio compound with high additional value is synthesized from cheap and easily available raw materials, the reaction conditions are mild, green and efficient, and a metal catalyst and an oxidizing agent are not required to be used.

Description

Technical field [0001] The invention relates to a method for synthesizing aryl trifluoromethylthio compounds, and belongs to the field of organic compound synthesis. Background technique [0002] Fluorine-containing functional groups have always been key structural units in various drugs and agrochemicals [1] , Trifluoromethylthio (CF 3 S) As an aromatic substituent, it plays an important role due to its strong electron withdrawing effect and high lipophilicity [2] . In recent years, the trifluoromethylation of aromatic hydrocarbons has made remarkable progress, but there are only a few methods that can be used to synthesize aryl trifluoromethylthio compounds, usually through trifluoromethyl mercaptan and aryl groups. Nucleophilic reaction of halide [3] . However, these methods require high temperature, expensive reagents and low reactivity of electron-rich aromatic substituents. These shortcomings limit the practicality of these synthetic methods. [0003] 【references】 [0004] [...

Claims

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Application Information

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IPC IPC(8): C25B3/00
CPCC25B3/00
Inventor 戴建军滕鑫鑫李晨光徐俊许华建
Owner HEFEI UNIV OF TECH
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