Hydrochloric Acid → 4-Bromo-3-fluoro-4'-methoxybenzophenone

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-bromo-3-fluorobenzoyl chloride (3.00 g, 12.6 mmol) and anisole (1.65 mL, 1.65 g, 15.2 mmol, 1.20 eq) in DCM (30 mL) at −5° C. was added, portion-wise, over 5 minutes, AlCl3 (2.54 g, 19.0 mmol, 1.50 eq) as a powder. The reaction was stirred at −5° C. for 2 h. The reaction was poured onto a mixture of 1 N HCl (100 mL) and ice (200 g) and stirred for 1 h. The DCM layer washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL) then dried (MgSO4) and concentrated. The resulting white solid was triturated with ˜100 mL hexanes, filtered and air-dried overnight to afford 3.26 g (83%) of compound 185. 1H NMR (400 MHz, DMSO-d6): δ 3.87 (s, 3 H), 7.11 (d, J=8.9 Hz, 2 H), 7.45 (d, J=8.9 Hz, 1H), 7.64 (d, J=8.9 Hz, 1 H), 7.78 (d, J=8.9 Hz, 2H), 7.91 (t, J=7.1 Hz, 1H).

Provenance & Evidence