Synthesis method of alpha-fluoroacrylate

A technology of fluoroacrylates and synthetic methods, which is applied in the preparation of carboxylic acid esters, chemical instruments and methods, and the preparation of carboxylic acid nitriles. It can solve the problems of harsh reaction conditions and high toxicity, and achieve short reaction time and high selectivity. , The effect of raw material economy

Pending Publication Date: 2021-10-08
CHUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0026] The present invention aims at the shortcomings existing in the existing synthesis methods of α-fluoroacrylates, such as harsh reaction conditions, the need to use highly toxic reagents, expensive metal catalysts, etc.

Method used

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  • Synthesis method of alpha-fluoroacrylate
  • Synthesis method of alpha-fluoroacrylate
  • Synthesis method of alpha-fluoroacrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1, the reaction formula of this embodiment is as follows:

[0038]

[0039] (1) Under air, m-bromobenzaldehyde (10mmol), diethyl fluoromalonate (1 equivalent), magnesium chloride (1 equivalent), N, N-diisopropylethylamine (DIPEA, 1 equivalent) was added Add 50 mL of anhydrous tetrahydrofuran to a 100 mL round bottom flask, and react under microwave conditions at 60°C for 30 minutes.

[0040] (2) adding ethyl acetate to the material obtained in step (1) and fully mixing, using short silica gel column chromatography, the eluent is a mixture of sherwood oil and ethyl acetate, the separation yield is 98%, and the product purity is 100%. Product Z:E = 35:1.

Embodiment 2

[0042] The reaction formula of this embodiment is as follows:

[0043]

[0044](1) Under air, m-cyanobenzaldehyde (10mmol), diethyl fluoromalonate, magnesium chloride (1 equivalent), N, N-diisopropylethylamine (DIPEA, 1 equivalent) were added as 100mL Add 50 mL of anhydrous tetrahydrofuran to a round bottom flask, and react under microwave conditions at 60°C for 30 minutes.

[0045] (2) Add ethyl acetate to the material obtained in step (1) and fully mix, use short silica gel column chromatography, the eluent is a mixture of sherwood oil and ethyl acetate, the separation yield is 97%, and the product purity is 100%. Product Z:E = 32:1.

Embodiment 3

[0047] The reaction formula of this embodiment is as follows:

[0048]

[0049] (1) Under air, perillaldehyde (10mmol), diethyl fluoromalonate (1 equivalent), magnesium chloride (1 equivalent), N, N-diisopropylethylamine (DIPEA, 1 equivalent) were added when Add 50 mL of anhydrous tetrahydrofuran to a 100 mL round bottom flask, and react under microwave conditions at 60° C. for 30 minutes.

[0050] (2) Add ethyl acetate to the material obtained in step (1) and fully mix, use short silica gel column chromatography, the eluent is a mixture of sherwood oil and ethyl acetate, the separation yield is 96%, and the product purity is 100%. Product Z:E = 30:1.

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Abstract

The invention belongs to the field of organic synthesis, and discloses a synthesis method of alpha-fluoroacrylate. The method comprises the following steps: taking aldehyde and diethyl fluoromalonate as raw materials, and reacting in a tetrahydrofuran solvent according to the following reaction formula under the conditions of magnesium chloride, N, N-diisopropylethylamine and microwave heating to obtain an alpha-fluoroacrylate compound with Z configuration. According to the invention, the alpha-fluoroacrylate synthesized by the method disclosed by the invention is simple in reaction operation, high in reaction yield and high in cis-trans proportion of the product olefin; reagents required by the reaction are low in price, and reagents with high toxicity and expensive metal catalysts are not required to be used; and the method is wide in substrate compatibility, economical and low in cost.

Description

technical field [0001] The invention relates to compound preparation and belongs to the field of organic synthesis. It specifically relates to the synthesis method of α-fluoroacrylate. Background technique [0002] α-Fluoroacrylate is a kind of important organic structure skeleton, widely exists in various bioactive molecules and drug molecules, such as analgesic, anticonvusant, respiratory drug, antitumor agent, Antitumor agents, anti Anti-inflammatory agents, anti-infective drugs Anti-infectious, (Formula 1). Therefore, the synthesis of α-fluoroacrylate has extremely important value. [0003] [0004] Formula 1. Active drug molecule containing α-fluoroendenoic acid [0005] At present, there are mainly two types of methods for the synthesis of α-fluoroacrylates, traditional organic synthesis reactions and transition metal catalyzed methods. The method reported as formula (1) uses ethyl dibromofluoroacetate and aldehydes under the reaction condition of 4 equivalents ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/343C07C253/30C07D213/55C07D307/54C07D307/79C07D319/18C07D333/24C07J1/00C07C69/65C07C255/57C07C69/734
CPCC07C67/343C07C253/30C07J1/0011C07D319/18C07D307/79C07D307/54C07D333/24C07D213/55C07C2601/16C07C69/65C07C255/57C07C69/734
Inventor 陆晓雨葛梦圆陈星珂
Owner CHUZHOU UNIV
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