Ammonium Chloride → 1-(4-Bromo-2-fluorophenyl)ethan-1-one

Participants

Reaction Steps

4-[(4-Bromo-2-fluorophenyl)carbonyl]morpholine (5.06 g, 17.6 mmol, 1.00 equiv) was dissolved in 150 mL of THF and the resultant solution was cooled to 0° C. Methyl magnesium bromide (17.6 mL, 3.0 M in Et2O, 52.7 mmol, 3.00 equiv) was added over 5 minutes via syringe. The reaction mixture was maintained for 30 minutes, an additional portion of methyl magnesium bromide was added (10 mL, 29.9 mmol, 1.70 equiv) and the reaction mixture was allowed to warm to room temperature. After an additional 1.5 h, the reaction mixture was poured into saturated NH4Cl. The mixture was diluted with EtOAc and the phases were separated. The organic phase was washed with 1N HCl, saturated NaHCO3, and saturated NaCl, then dried over Na2SO4, filtered and concentrated en vacuo. The resulting residue was purified by column chromatography (40 g SiO2, 0→10% EtOAc/Hexanes) to afford 2.59 g (68%) of a colorless oil. 1H NMR (CDCl3) δ 7.79 (t, J=8.2 Hz, 1H), 7.42-7.36 (m, 2H), 2.66 (d, J=5.0 Hz, 3H).

Provenance & Evidence