Boron tribromide → 1-[2,4-Dihydroxy-3-(3-phenylpropyl)phenyl]ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of 10.0 g (33.5 mmol) of 1-[2,4-dimethoxy-3-(3-phenylpropyl)phenyl]ethanone from the preceding example in 250 mL of dichloromethane was stirred at -50° C. while 67 mL (67 mmol) of 1m boron tribromide in dichloromethane was added over a 15 min period. The reaction mixture was stirred at -50° C. for 1 hr and at room temperature for 3 days before being poured onto ice. Work-up with 9:1 dichloromethanemethanol in the usual manner gave a product which was a chromatographed on silica gel. Elution with hexane-ether mixtures gave 6.69 g (74%) of the title compound as a solid. Recrystallization of a sample from ether-hexane gave colorless solid, mp 120°-122° C.

Provenance & Evidence