Potassium Carbonate → Benzyl (2,5-dibromophenoxy)propionate

Participants

Reaction Steps

2,5-Dibromophenol (53 g) and benzyl 2-bromopropionate (48.6 g) in methyl iso-butyl ketone (250 ml) containing suspended potassium carbonate (13.8 g) was heated under reflux with stirring overnight. The mixture was cooled to 40°, 5% sodium hydroxide solution (100 ml) was added, and the mixture was stirred to dissolve the solid potassium bromide. The aqueous phase was separated with fresh methyl iso-butyl ketone (50 ml). The combined extracts were washed with water (50 ml), dried, and evaporated under reduced pressure. The residue was distilled and the benzyl (2,5-dibromophenoxy)propionate collected at 180°-185°/0.5 Torr. On cooling, the distillate solidified and had a melting point of 52° C. Compounds 1, 5, 6, 14 to 16, 18 to 20, 22 and 23 were made by a similar procedure.

Provenance & Evidence