Phenacyl bromide → HCID 23143333, compound

Participants

Reaction Steps

A mixture of N-[2-(4-chlorophenyl)ethyl]thiourea (108 mg), 2-bromo-1-phenylethanone (100 mg) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 1 hr. Sodium hydride (60% in oil, 40 mg) was added to this mixture under ice-cooling, allowed to warm to room temperature and stirred for 1 hr. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (159 mg) was added to the reaction mixture under ice-cooling, and the mixture was allowed to warm to room temperature and further stirred for 1 hr. The reaction mixture was poured into aqueous potassium dihydrogenphosphate solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated and the residue was purified by preparative HPLC (gradient cycle A) to give the title compound (113 mg, yield 39%) as a yellow oil.

Provenance & Evidence