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

Temperature

-5 °C

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 was 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, 3H), 7.11 (d, J=8.9 Hz, 2H), 7.45 (d, J=8.9 Hz, 1H), 7.64 (d, J=8.9 Hz, 1H), 7.78 (d, J=8.9 Hz, 2H), 7.91 (t, J=7.1 Hz, 1H).

1. stirringstirred for 1 h
2. washThe DCM layer was washed with saturated aq. NaHCO3 (100 mL) and brine (100 mL)
3. dry with materialthen dried (MgSO4)
4. concentrationconcentrated
5. customThe resulting white solid was triturated with ˜100 mL hexanes
6. filtrationfiltered
7. customair-dried overnight

ORD record

ord-87553e4513324219822041c7498da82e

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560589B2