Ethanol → Ethyl 3-bromo-2,2,3,3-tetrafluoropropionate

Reaction equation

[Br:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>>[Br:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4]([O:6][CH2:16][CH3:17])=[O:5]

Participants

Reactant 3

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 133289113-Bromo-2,2,3,3-tetrafluoropropanoic acid

Product 1

HCID 23233362Ethyl 3-bromo-2,2,3,3-tetrafluoropropionate

Procedure

To a solution of 7.0 g (31 mmol) of 3-bromo-2,2,3,3-tetrafluoropropionic acid in 40 ml of ethanol was added 1.0 ml of concentrated sulfuric acid, and the mixture was heated under reflux for 8 hours and then distilled under ordinary pressure to give an ethanolic solution of ethyl 3-bromo-2,2,3,3-tetrafluoropropionate. Ammonia gas was blown into the solution, which was left at room temperature overnight and then concentrated under reduced pressure to give 5.6 g of 3-bromo-2,2,3,3-tetrafluoropropionamide as a white solid.