Bromine → 2-Bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethan-1-one

Participants

Reaction Steps

A solution of bromine (96 ml) in chloroform (427 ml) was added dropwise at 10°-15° C. over 1.5 hours to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (477.2 g; prepared in a similar manner to that described above) in a mixture of methanol (643 ml) and chloroform (107 ml). After the addition was complete, the mixture was stirred at ambient temperature for 3 hours, then poured into ice-water (21). The aqueous layer was separated and washed with dichloromethane (3×500 ml), then the combined organic solutions were washed with saturated aqueous sodium hydrogencarbonate solution (2×400 ml) and water (500 ml), dried over calcium chloride, and the, solvents were removed in vacuo to leave 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone as an orange oil (593.5 g) which was used without purification.

Provenance & Evidence