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Method for synthesizing compounds containing vinyl trifluoromethyl structure

A technology of vinyl trifluoromethyl and trifluoromethyl sources is applied in electrolytic process, electrolytic components, electrolytic organic production, etc., to achieve the effects of low price, simple operation and mild reaction conditions

Inactive Publication Date: 2019-07-05
WUYI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, until now, there have been few reports on the synthesis of compounds containing vinyltrifluoromethyl structures via electrochemical routes.

Method used

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  • Method for synthesizing compounds containing vinyl trifluoromethyl structure
  • Method for synthesizing compounds containing vinyl trifluoromethyl structure
  • Method for synthesizing compounds containing vinyl trifluoromethyl structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 (E)-(3,3,3-trifluoroprop-1-en-1-yl)benzene

[0025]

[0026] Take a three-neck round bottom flask, add 5 mL of dimethyl sulfoxide and 2.5 mL of dichloromethane, 74 mg (0.50 mmol) of cinnamic acid, 234 mg (1.5 mmol) of sodium trifluoromethylsulfinate, and 97 mg of tetra-n-butylammonium hexafluorophosphate (0.25mmol), with a carbon rod as the anode and a platinum sheet as the cathode, the electrochemical reaction was stirred at room temperature for 3 hours under a current of 7mA. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, and 5 mL of saturated brine was added for washing. After separation, the organic phase was collected, and the aqueous phase was extracted 3 times with ethyl acetate, each time the amount of ethyl acetate was 5 mL, and the organic phase was combined. Anhydrous sodium sulfate was added for drying, the solvent was distilled off under reduced pressure, and the product was obtain...

Embodiment 2

[0028] Synthesis of Example 2 (E)-1-methyl-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene

[0029]

[0030] Take a three-neck round bottom flask, add 5 mL of dimethyl sulfoxide, 2.5 mL of dichloromethane, 81 mg (0.50 mmol) of (E)-3-(p-tolyl)acrylic acid, and 234 mg (1.5 mmol) of sodium trifluoromethylsulfinate . 97 mg (0.25 mmol) of tetra-n-butylammonium hexafluorophosphate, with a carbon rod as an anode and a platinum sheet as a cathode, and electrochemically reacted at room temperature for 3 hours under stirring at a current of 7 mA. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, and 5 mL of saturated brine was added for washing. After separation, the organic phase was collected, and the aqueous phase was extracted 3 times with ethyl acetate, each time the amount of ethyl acetate was 5 mL, and the organic phase was combined. Anhydrous sodium sulfate was added for drying, the solvent was distilled off under reduced pressure, and the pr...

Embodiment 3

[0032] Synthesis of Example 3 (E)-1-methoxy-4-(3,3,3-trifluoroprop-1-en-1-yl)benzene

[0033]

[0034] Take a three-neck round bottom flask, add 5 mL of dimethyl sulfoxide, 2.5 mL of dichloromethane, 89 mg (0.50 mmol) of (E)-3-(4-methoxyphenyl) acrylic acid, and 234 mg of sodium trifluoromethylsulfinate (1.5mmol), 97mg (0.25mmol) of tetra-n-butylammonium hexafluorophosphate, with a carbon rod as the anode and a platinum sheet as the cathode, and stirred at room temperature for an electrochemical reaction at 7mA for 3 hours. After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction, and 5 mL of saturated brine was added for washing. After separation, the organic phase was collected, and the aqueous phase was extracted 3 times with ethyl acetate, each time the amount of ethyl acetate was 5 mL, and the organic phase was combined. Anhydrous sodium sulfate was added to dry, the solvent was distilled off under reduced pressure, and the product was ob...

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Abstract

The invention belongs to the field of organic substance synthesis, specifically relates to a method for synthesizing compounds containing a vinyl trifluoromethyl structure, and particularly relates toa method for synthesizing compounds containing a vinyl trifluoromethyl structure through electrochemical decarboxylation trifluoro-methylation. Specifically, in a solvent, alpha, beta-unsaturated carboxylic acids are taken as the raw materials, electrolyte and a trifluoromethyl source are added; through electrochemical anode oxidation reactions, compounds containing a vinyl trifluoromethyl structure are prepared, the anode is a carbon rod, and the cathode is a platinum sheet. Compared with reported methods, the provided method does not use any metal catalyst or external oxidizing agent; the used electrolyte and trifluoromethyl source are cheap, nontoxic, and odorless; the post treatment is simple, the method is suitable for industrial production, the reaction conditions are mild, the operation is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, in particular to a method for synthesizing a compound containing a vinyl trifluoromethyl structure, in particular to a method for synthesizing a compound containing a vinyl trifluoromethyl structure by electrochemical decarboxylation and trifluoromethylation . Background technique [0002] Since the trifluoromethyl group can significantly change the properties of the molecule, such as stability, lipophilicity, and bioavailability, etc., the development of efficient and sustainable trifluoromethylation reactions to introduce trifluoromethyl functional groups into various organic Molecules have important research value in the fields of drug development, new material synthesis and life sciences. Vinyl trifluoromethyl groups have always been considered as an important part of pharmaceutical agents, and compounds containing vinyl trifluoromethyl structures are basically unnatural and need to...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 黄玉冰邹子荣洪焕良覃永威李亦彪
Owner WUYI UNIV
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