Hydrochloric Acid → Bromopentafluorobenzene

Participants

Reaction Steps

In a 2 l, N2 purged flask were combined hexafluorobenzene (145 g), FeCl2 (0.8 g) and THF (600 ml). The solution was cooled to 0°-5° C., and ethyl magnesium bromide (3.12M in Et2O, 500 ml) was then added dropwise. After the addition was complete, the reaction mixture was stirred for one-half hour. A solution of bromine (125g) n methylene chloride (250 ml) was then added dropwise to the cold (0°-5° C.) reaction mixture. After stirring 15 minutes, 4N HCl was added until all solids were dissolved. The two phases were separated and the organics were washed sequentially with water, aqueous sodium bicarbonate and brine. After drying over sodium sulfate, the mixture was distilled providing 160 g of C6F5Br (83% yield).

Provenance & Evidence