2-Fluoroacryloyl chloride → Perfluoro-2,3-dimethyl-2-butyl alpha-fluoroacrylate

HRID 1614786Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]([C:15]([F:18])([F:17])[F:16])([O-:14])[C:4]([F:13])([C:9]([F:12])([F:11])[F:10])[C:5]([F:8])([F:7])[F:6].[K+].[F:22][C:23](=[CH2:27])[C:24](Cl)=[O:25]>C(OCC)C>[F:22][C:23](=[CH2:27])[C:24]([O:14][C:3]([C:15]([F:16])([F:17])[F:18])([C:4]([F:13])([C:5]([F:8])([F:7])[F:6])[C:9]([F:12])([F:11])[F:10])[C:2]([F:19])([F:20])[F:1])=[O:25]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 213.6 g (0.571 mol) of potassium perfluoro-2,3-dimethyl-2-butanolate in 250 ml of dry diethyl ether was added dropwise with stirring at a temperature of 25° C. to a solution of 62 g (0.571 mol) of α-fluoroacryloyl chloride (obtained according to Example 4) in 100 ml of dry diethyl ether in the course of 1 hour, and a colorless solid precipitated. The reaction mixture was stirred at a temperature of 25° C. for a further hour, and the solid was filtered off. The filtrate had added to it 0.01 g of hydroquinone monomethyl ether and was then distilled under reduced pressure. 167 g (72 percent of theory) of perfluoro-2,3-dimethyl-2-butyl α-fluoroacrylate having a boiling point of 43° C. (under 20 mbar) were obtained.

Workup

customa colorless solid precipitated
filtrationthe solid was filtered off
additionThe filtrate had added to it 0.01 g of hydroquinone monomethyl ether
distillationwas then distilled under reduced pressure

Sources & evidence

ORD record: ord-7ac4d01bcb7b4eb59619e154d5329706
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05198925

Reaction notes

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