Hydrochloric Acid → HCID 68654435, compound

Participants

Reaction Steps

The demethylation procedure described for 2 was employed. To a stirred solution of (4-bromo-3-fluorophenyl)[3-(methyloxy)phenyl]methanone (1.0 g, 2.5 mol) in toluene (50 mL) was slowly added AlCl3 (1.3 g, 9.7 mol) via a powder addition funnel under a nitrogen atmosphere at room temperature. The stirred reaction mixture was heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and then poured into 10% aqueous HCl (200 mL). Standard work-up yielded 0.935 g (100%) of the title compound 196 as a tan solid. 1H NMR (300 MHz, CDCl3): δ 7.71 and 7.68 (dd, J1=6.6 Hz, J2=6.6 Hz, 1H), 7.60 and 7.57 (dd, J1=8.7 Hz, J2=1.5 Hz, 1H), 7.50 and 7.47 (dd, J1=8.1 Hz, J2=1.2 Hz, 1H), 7.41-7.31 (m 3H), 7.15 and 7.13 (dd, J1=7.8 Hz, J2=1.8 Hz, 1H), 5.93(s, 1H).

Provenance & Evidence