Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper

A technology for synthesizing trifluoroethyl sulfide and aromatic hydrocarbons, which can be used in the preparation of sulfides, organic chemistry, etc., can solve the problems of inaccessibility and expensiveness of aromatic thiophenols, and achieves the effects of good adaptability, high yield, and simple reaction operation.

Inactive Publication Date: 2016-04-13
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But because aromatic hydrocarbon thiophenol is difficult to get, expensive, and has strong stink, therefore invents a kind of metho

Method used

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  • Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper
  • Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper
  • Method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper

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Experimental program
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Effect test

Embodiment 1

[0020] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050mmol cuprous iodide, 0.10mmol1,10-phenanthroline, 0.50mmol2-iodobenzoic acid methyl ester, 1.0mmol Sulfur powder, 1.0mmol 2,2,2-trifluoroiodoethane, 1.5mmol sodium borohydride, finally add 5mL N,N-dimethylformamide, stir and react in a closed system at 80°C for 16h, cool to room temperature, and use Diethyl ether was extracted 3 times, 10 mL each time, the organic phases were combined, washed 3 times with distilled water, the organic phase was dried with anhydrous magnesium sulfate, filtered, and then rotary evaporated to remove the organic solvent; Elution was carried out with alkane as the eluent to obtain methyl 2-(2,2,2-trifluoroethylthio)benzoate (isolated yield 83%). 1 HNMR (400MHz, CDCl 3 )δ7.96(d,J=8.6Hz,1H),7.59–7.42(m,2H),7.36–7.29(m,1H),3.96(s,3H),3.60(q,J=9.7Hz,2H ). 19 FNMR (376MHz, CDCl 3 )δ-65.2 (t, J=9.7Hz, 3F). GC-MSm / z250(M + ).

Embodiment 2

[0022] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050mmol cuprous iodide, 0.10mmol1,10-phenanthroline, 0.50mmol2-cyanoiodobenzene, 1.0mmol sulfur powder, 1.0mmol 2,2,2-trifluoroiodoethane, 1.5mmol sodium borohydride, and finally add 5mL N,N-dimethylformamide, stir and react in a closed system at 80°C for 16h, cool to room temperature, and diethyl ether Extract 3 times, 10mL each time, combine the organic phases, wash 3 times with distilled water, dry the organic phases with anhydrous magnesium sulfate, filter, and then rotary evaporate to remove the organic solvent; Elution was performed as eluent to give 2-(2,2,2-trifluoroethylthio)benzonitrile (isolated yield 76%). 1 HNMR (400MHz, CDCl 3 )δ7.77–7.65(m,2H),7.60(t,J=7.7Hz,1H),7.45(t,J=7.8Hz,1H),3.58(q,J=9.5Hz,2H). 19 FNMR (376MHz, CDCl 3 )δ-66.1 (t, J=9.4Hz, 3F). GC-MSm / z217(M + ).

Embodiment 3

[0024] In a nitrogen atmosphere, put a polytetrafluoroethylene magnet in a reactor, then add 0.050mmol cuprous iodide, 0.10mmol1,10-phenanthroline, 0.50mmol1-iodonaphthalene, 1.0mmol sulfur powder, 1.0mmol 2,2,2-trifluoroiodoethane, 1.5mmol sodium borohydride, finally add 5mL N,N-dimethylformamide, stir and react in a closed system at 85°C for 16h, cool to room temperature, and extract with ether for 3 times, 10 mL each time, combined the organic phases, washed 3 times with distilled water, dried the organic phases with anhydrous magnesium sulfate, filtered, and then rotary evaporated to remove the organic solvent; The solvent was removed for elution to obtain 1-(2,2,2-trifluoroethyl)naphthalene sulfide (isolated yield 92%). 1 HNMR (400MHz, CDCl 3 )δ8.52(d,J=8.5Hz,1H),7.91(m,3H),7.63(m,2H),7.48(t,J=7.7Hz,1H),3.49(q,J=9.7Hz, 2H). 19 FNMR (376MHz, CDCl 3 )δ-66.0 (t, J=9.8Hz, 3F). GC-MSm / z242(M + ).

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Abstract

The invention discloses a method for carrying out catalytic synthesis on arene 2,2,2-trifluoro-ethyl sulfide through copper. The method includes the steps that copper iodide is adopted as a catalyst, diimine is adopted as a bidentate ligand, arene halogen, powdered sulfur and 2,2,2-trifluoro-ethyl iodide are adopted as reactants, sodium borohydride is adopted as a reducing agent, stirring is conducted for 1-24 hours at the temperature of 80 DEG C to 95 DEG C in an N,N-dimethyl formamide solvent, aftertreatment is conducted on reaction liquid after the reaction is completed, and the arene 2,2,2-trifluoro-ethyl sulfide compound is obtained. The synthesis method has the advantages that the catalyst is low in price, easy to obtain and low in toxicity, the raw materials are easy to obtain, operation is easy and convenient, and the universality of functional groups is good.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a copper-catalyzed method for synthesizing aromatic hydrocarbon 2,2,2-trifluoroethyl sulfide. Background technique [0002] Fluorine-containing groups have strong electron-withdrawing properties and high lipophilicity, and exhibit many very unique physical and chemical properties. After introducing fluorine-containing groups into the molecule, it will obviously change the polarity of the molecule, reduce the pKa value and improve the membrane permeability, and also affect the metabolic pathway and pharmacokinetic characteristics of the molecule. Among many compounds containing fluorine groups, compounds containing 2,2,2-trifluoroethylthio have received special attention, and many molecules with biological activity contain this group. However, so far, there are few reports on the synthesis of arene 2,2,2-trifluoroethyl sulfide, which is mainly obtained through the rea...

Claims

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Application Information

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IPC IPC(8): C07C323/03C07C319/14C07C323/62C07C323/20C07C323/09
CPCC07C319/14C07C323/03C07C323/62C07C323/20C07C323/09
Inventor 翁志强陈守雄吴伟张云霄
Owner FUZHOU UNIV
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