Water → HCID 67015589, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 3-(4-bromo-phenyl)-1-(4-methoxy-phenyl)-3-o-tolyl-propan-1-one (214 mg) in dichloromethane (5.1 ml) under argon was cooled to −78° C. A solution of BBr3 (2.09 ml, 1 M in dichloromethane) was added dropwise. The mixture was stirred at −78° C. for 45 min, at 0° C. for 4 h and at room temperature for 30 min. Since the reaction was not complete, the mixture was again cooled to −78° C. and a solution of BBr3 (1 ml, 1 M in dichloromethane) was added. The mixture was stirred at −78° C. for 30 min and at 0° C. for 4.5 h. Water and a saturated aqueous NaHCO3 solution were added and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried using MgSO4, filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 7:3) to give the title compound (21 mg) as a light brown solid, MS (ESI+): m/z=394.8 [M−H]−.

Provenance & Evidence