Bromine → 1,2-Benzenediol, 4-bromo-3-fluoro- (9CI)

Participants

Reaction Conditions

Reaction Steps

3-Fluorocatechol (7.2 g) in 50 ml of carbon tetrachloride and 40 ml of chloroform are treated at -10° C. within 10 minutes with a solution of 2.88 ml of bromine in 30 ml of carbon tetrachloride. After stirring at -10° C. for 1 hour the reaction mixture is filtered. The residual solid is washed with a small amount of cold carbon tetrachloride and dried. There are obtained 6.30 g of 4-bromo-3-fluorocatechol as a white powder. This is treated with 6.0 ml of diphenylchloromethane and heated to 130° C. within 1 hour. Subsequently, the product is distilled at 135° C./0.05 Torr and recrystallized from ethanol. There are obtained 6.40 g of 5-bromo-4-fluoro-2,2-diphenyl-1,3-benzodioxol as a white crystalline powder of m.p. 61.5°-63° C.

Provenance & Evidence