Boron tribromide → HCID 14239188, compound

Participants

Reaction Steps

A solution of 1.6 g (0.6 mL) of boron bromide in 5 mL of dry methylene chloride was added dropwise to a stirred suspension of 200 mg of the methoxyaldehyde 38 in 50 mL of dry CH2Cl2 at -78° C. The stirred suspension was allowed to warm to room temperature and stirred for an additional 6 hours. The mixture was cooled in an ice bath and about 5 mL of ice-water was added after 30 minutes the methylene chloride layer was separated under nitrogen. The aqueous brown suspension was cooled in an ice-bath and made alkaline with 15 mL of 10% sodium hydroxide under nitrogen. The dark red solution was taken to pH 7-8 with the aid of acetic acid, sodium bicarbonate solution. The brown precipitate was collected on a filter, washed with water and dried. The dry solid was triturated with methylene chloride-hexane (1:1) and filtered to give the desired crude phenolic aldehyde. Wt. 170 mg, m.p. 346°-349° C.

Provenance & Evidence