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Fluorination method of vinyl carboxylic acid

A technology of alkenyl carboxylic acid and fluorination, applied in chemical instruments and methods, organic chemistry, preparation of organic compounds, etc., can solve the problem of unsaturated carboxylic acid that no one has reported

Active Publication Date: 2011-10-19
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The decarboxylation fluorination of saturated carboxylic acids has been reported very early ((a) Patrick, T.B., Johri, K, K., White, D.H., J.Org.Chem.1983, 48, 4158; (b) Patrick, T.B. , Johri, K, K., White, D.H., Bertrand, W.S., Mokhtar, R., Kilbourn, M.R., Welch, M.J., Can.J.Chem.1986, 64, 138), for the decarboxylation of unsaturated carboxylic acids Chlorination and chlorination have also been realized (Naskar, D., Roy, S., Tetrahedron 2000, 56, 1369), but no one has reported the electrophilic fluorination decarboxylation of unsaturated carboxylic acids

Method used

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  • Fluorination method of vinyl carboxylic acid
  • Fluorination method of vinyl carboxylic acid
  • Fluorination method of vinyl carboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079]

[0080] In a reaction tube equipped with a built-in reflux condenser, add 3,3-diphenylacrylic acid (112mg, 0.5mmol), Selectfluor (213mg, 0.6mmol), nickel acetate dihydrate (124mg, 0.5mmol), 2mL of tetrachloromethane carbonized carbon, 3 mL of water, 0.5 mL of trifluoroacetic acid, stirred, and heated to reflux for 40 hours. After cooling to room temperature, it was first neutralized to weak alkalinity with saturated aqueous sodium bicarbonate solution, and then extracted with dichloromethane. The organic layer was concentrated through a column to obtain 79 mg of a colorless liquid with a yield of 80%.

Embodiment 2

[0082]

[0083] Add 3,3-diphenylacrylic acid (112mg, 0.5mmol), Selectfluor (532mg, 1.5mmol), 5mL water, and 1mL trifluoroacetic acid in sequence in a 20mL reaction tube equipped with a built-in reflux condenser, stir, and heat to reflux 60 hours. After cooling to room temperature, it was first neutralized to weak alkalinity with saturated aqueous sodium bicarbonate solution, and then extracted with dichloromethane. The organic layer was concentrated through a column to obtain 104 mg of a colorless liquid with a yield of 89%.

Embodiment 3

[0085]

[0086] Add 3-(4-nitrophenyl)acrylic acid (104mg, 0.5mmol), Selectfluor (532mg, 1.5mmol), 5mL water, 1mL trifluoroacetic acid in turn in a 20mL reaction tube equipped with a built-in reflux condenser, and stir , heated to reflux for 60 hours. After cooling to room temperature, it was first neutralized to weak alkalinity with saturated aqueous sodium bicarbonate solution, and then extracted with dichloromethane. The organic layer was concentrated through a column to obtain 53 mg of a colorless liquid with a yield of 43%.

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Abstract

The invention relates to a decarboxylation and fluorination method of vinyl carboxylic acid. In the method, in an aqueous or polar organic solvent or a mixed solvent of aqueous and polar organic solvents, vinyl carboxylic acid, an additive and an electrophilic fluorinating reagent are reacted at room temperature-reflux temperature so as to synthesize monofluoro olefin, allyl fluoride, difluoro alkyl substituted alcohol, mono-difluoro alkyl substituted alcohol, monofluoro alkyl substituted epoxide, beta-monofluoro / difluoro substituted cyclic lactone or beta-monofluoro substituted unsaturated cyclic lactone compounds. The structural formula of vinyl carboxylic acid is shown in the specification. According to the method in the invention, raw materials are available, reaction is simple and convenient, and the method can be used for preparing compounds which are difficult to prepare by using a common method.

Description

technical field [0001] The present invention relates to the fluorination method of alkenyl carboxylic acid, further say the electrophilic fluorination reaction of a kind of alkenyl carboxylic acid, and utilize these reactions to monofluoroalkene, allyl fluoride, difluoroalkyl substitution Alcohols, double monofluoroalkyl substituted alcohols, monofluoroalkyl substituted epoxy compounds, β-monofluorosubstituted, difluorosubstituted cyclic lactones and β-monofluorosubstituted unsaturated cyclic lactones synthesis. Background technique [0002] Fluorine-containing drugs and pesticides are generally compounds containing a single fluorine atom or a few fluorine groups such as difluoromethyl and trifluoromethyl. A large number of facts show that introducing fluorine atoms or fluorine-containing groups into molecules can change the physiological activity of molecules. This is mainly due to the unique properties of fluorine atoms, such as difluoromethyl (CF 2 H) and hydroxymethyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C22/08C07C17/363C07C33/46C07C29/62C07C205/26C07C201/12C07D303/08C07D301/02C07D307/58C07D209/30C07D215/20
Inventor 胡金波何正标
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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