(4-Bromo-3-fluorophenyl)(morpholin-4-yl)methanone → 1-(4-Bromo-3-fluorophenyl)ethan-1-one

Participants

Reaction Steps

To a 0° C. solution containing 8.62 g of 4-[(4-bromo-3-fluorophenyl)carbonyl]morpholine (30 mmols) in 150 mL THF was added 15 mL of methylmagnesium bromide (45 mmols, 3M solution in Et2O). The reaction mixture was allowed to warm slowly to ambient temperature. After 18 h the reaction mixture was quenched with 20 mL saturated aqueous NH4Cl solution. The layers were separated, and the organic layer was dried over MgSO4, filtered through a frit, and concentrated. The crude product was purified by silica gel chromatography (120 g redisep column, silica 40 um, 60A, 85 ml/min, A: EtOAc, B: hexanes, A: 8% for 14 min) to give 2.40 g (37%) of title compound as a yellow oil.

Provenance & Evidence