Boron tribromide → HCID 22123618, compound

Participants

Reaction Steps

To a solution of 7-methoxy-3-(4-methoxyphenyl)-3-methyl-4-(9-pentylthiononyl)thiochroman (230 mg, 0.435 mmol) in dry dichloromethane (20 ml) was added dropwise 1M solution of boron tribromide in dichloromethane (3.04 ml, 3.04 mmol) at -78° C. and stirred at the same temperature for one hour. Then the reaction mixture was warmed to room temperature and stirring was continued for additional 10 hours. The reaction mixture was quenched with water and then diluted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen sulfide solution and water, dried over magnesium sulfate, filtered and evaporated. The concentrate was subjected to flash silica gel chromatography (hexane:ethyl acetate=9:1) to obtain 178 mg (yield: 82%) of the title compound as a colorless oil.

Provenance & Evidence