Preparation method of fluoride and intermediate thereof

A compound, thionyl fluoride technology, applied in the field of preparation of fluoride and its intermediates, can solve the problems of strong corrosion, cumbersome operation, and low yield

Active Publication Date: 2020-12-15
中科利民(浙江)新能源有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0024] The technical problem to be solved by the present invention is to provide a preparation method of fluoride and its intermediates in order to overcome the defects of low yield, strong corrosion or complicated operation in the existing preparation method of fluoride

Method used

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  • Preparation method of fluoride and intermediate thereof
  • Preparation method of fluoride and intermediate thereof
  • Preparation method of fluoride and intermediate thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] [chemical formula 3]

[0125]

[0126] Select optically active [chemical formula 3] α-hydroxy carboxylate methyl ester as substrate, in the reactor, charge the [chemical formula 3] α-hydroxy carboxylate of 10.6g (100mmol, 1.00eq, photochemical purity more than 98.0%ee) Acetate methyl ester, and 11.1g (110mmol, 1.1eq) of triethylamine, after adding 100ml of solvent DMF (N,N-dimethylamide) and stirring at -15°C, then slowly bubbling 9.89g of (115mmol, 1.15eq) of SOF 2 Gas (thionyl fluoride gas), the internal temperature will increase with the amount of gas blown in. After 1h, intermediate II-1 is obtained. After testing, 19 FNMR (376MHz, reference substance is trifluorotoluene) δ62.11, 60.32 (two fluorine peaks).

[0127]

[0128] The mixed solution was heated to 100° C., and the reaction was completed after 2 hours, and the reaction conversion rate reached more than 95%. Then, the reaction-terminated liquid was directly distilled under reduced pressure, and the ...

Embodiment 2

[0145] Select optically active α-hydroxycarboxylate methyl ester as substrate, and charge [chemical formula 3] α-hydroxycarboxylate methyl ester and 5.55g (50mmol, 0.5eq) of triethylamine, then add 100ml of solvent DMF (N,N-dimethylamide) and stir evenly at -15°C, then slowly bubble 9.89g (115mmol, 1.15eq ) of SOF 2 Gas (thionyl fluoride gas), the internal temperature will increase with the amount of gas blown in. After 1 hour, the mixed solution is heated to 100 ° C. After 2 hours of reaction, the reaction conversion rate reaches more than 95%.

[0146] Then, the reaction-terminated liquid was directly distilled under reduced pressure, and the temperature of the distilled oil bath was 80° C., thereby obtaining 6.3 g of liquid (R)-methyl 2-fluoropropionate fraction product of [Chemical Formula 4]. The recovery rate was 60%. The chemical purity of the distillate was 1 The photochemical purity was above 95% as calculated by H NMR.

[0147] (R)-Methyl 2-fluoropropionate 19 F...

Embodiment 3

[0149]Select optically active [chemical formula 3] α-hydroxy carboxylate methyl ester as substrate, in the reactor, charge the [chemical formula 3] α-hydroxy carboxylate of 10.6g (100mmol, 1.00eq, photochemical purity more than 98.0%ee) Acetate methyl ester and 11.1g (110mmol, 1.1eq) of triethylamine, after adding 100ml of solvent DMF (N,N-dimethylamide) and stirring at -15°C, then slowly bubbling 9.89g ( 115mmol, 1.15eq) of SOF 2 Gas (thionyl fluoride gas), the internal temperature will increase with the amount of gas blown in. After 1 hour, the mixed solution is heated to 100 ° C. After 2 hours of reaction, the reaction conversion rate reaches more than 95%.

[0150] Then, the reaction-terminated liquid was directly distilled under reduced pressure, and the temperature of the distilled oil bath was 80° C., thereby obtaining 7.3 g of liquid (R)-methyl 2-fluoropropionate fraction product of [Chemical Formula 4]. The recovery rate was 65%. The chemical purity of the distillat...

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Abstract

The invention discloses a preparation method of fluoride and an intermediate thereof. The preparation method disclosed by the invention comprises the following step: in the presence of an alkaline reagent, carrying out a reaction of a compound III and thionyl fluoride in an organic solvent to obtain a compound shown as a formula I, according to the preparation method, the fluorosulfite compound isobtained with high yield, and the fluorosulfite compound has good functional group compatibility and substrate universality.

Description

technical field [0001] The invention relates to a preparation method of fluoride and its intermediate. Background technique [0002] Fluorine-containing compounds are a class of substances of great value in industry, and can be used as intermediates in the synthesis of plant protection agents or pesticides, especially photoactive α-fluorocarboxylates. Photoactive α-fluorocarboxylates are important intermediates in medicine, pesticides, and optical materials. [0003] In view of the importance of such fluorine-containing compounds, people continue to study and explore industrial fluorination methods that are easy to scale up, which can use cheap and easy-to-obtain raw materials and efficiently synthesize such fluorine compound intermediates. [0004] Patent CN101052612A (applicant is French Rhodes Chemical Company) discloses that thionyl chloride (SOCl 2 ) is prepared as chlorosulfite under the action of alkali, then it is converted into fluorosulfite by hydrogen fluoride (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C313/04C07C69/63C07C67/307C07C69/65C07C233/15C07C231/12C07J9/00C07C22/08C07C17/16C07C23/38C07B39/00
CPCC07C313/04C07C69/63C07C69/65C07C233/15C07J9/00C07C22/08C07C23/38C07B39/00C07C2601/16C07C2603/74C07B2200/07Y02E60/10
Inventor 董佳家柯森徐龙
Owner 中科利民(浙江)新能源有限公司
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