Carbon tetrabromide → 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide

Participants

Reaction Steps

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-hydroxyethyl)phenyl]butanamide (25 g), carbon tetrabromide (51 g), diethyl ether (140 mL) and tetrahydrofuran (140 mL) was cooled in ice and treated with triphenylphosphine (39.3 g), portionwise. When addition of the phosphine was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The precipitate was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel, eluted with dichloromethane to give 16.2 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide as a white solid.

Provenance & Evidence