Dimethylformamide → 2H-Perfluoroisopropyl 2-fluoroacrylate
Reaction equation
[F:1][C:2](=[CH2:6])[C:3]([OH:5])=[O:4].CN(C)C=O.S(Cl)(Cl)=O.C(N(CCCC)CCCC)CCC.[F:29][C:30]([F:38])([F:37])[CH:31](O)[C:32]([F:35])([F:34])[F:33]>C1(C)C(C)=CC=CC=1>[F:1][C:2](=[CH2:6])[C:3]([O:5][CH:31]([C:32]([F:35])([F:34])[F:33])[C:30]([F:38])([F:37])[F:29])=[O:4]Participants
7
Conditions
- Temperature
- 80 °C
Procedure
107 g (1 mol) of the ammonium salt of α-fluoroacrylic acid are mixed with 14.5 g (0.2 mol) of dimethylformamide and 0.6 liter of xylene, and 131 g (1.1 mol) of thionyl chloride are added dropwise to the mixture in the course of one hour; the mixture is then warmed at a temperature of 80° C. for two hours. After cooling to a temperature of 0° C., a mixture of 204 g (1.1 mol) of tributylamine and 185 g (1.1 mol) of hexafluoroisopropanol is added to the reaction mixture in the course of 30 minutes. The mixture is then stirred at a temperature of 30° C. for a further hour and is finally filtered. The filtrate is distilled under a pressure of 270 mbar and hexafluoroisopropyl α-fluoroacrylate is obtained as a colorless liquid.
Workup
- additionare added dropwise to the mixture in the course of one hour
- temperatureAfter cooling to a temperature of 0° C.
- additionis added to the reaction mixture in the course of 30 minutes
- filtrationis finally filtered
- distillationThe filtrate is distilled under a pressure of 270 mbar
Sources & evidence
- ORD record
- ord-09ce754421b5441c80a867e33cea86ec
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04863236
Reaction notes
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