Hydrochloric Acid → (4-Bromophenyl)(4-hydroxyphenyl)methanone

Participants

Reaction Steps

To a stirred solution of (4-bromophenyl)[4-(methyloxy)phenyl]methanone (1) (27.0 g, 0.93 mol) in toluene (400 mL) was slowly added AlCl3 (32.0 g, 0.23 mol, 2.5 eq) via a powder addition funnel under a nitrogen atmosphere at RT. The stirred reaction mixture was heated at reflux for 5 h under a blanket of N2. The reaction mixture was allowed to cool to RT and then poured into 10% aqueous HCl (1 L). The reaction mixture was transferred to a separatory funnel and the layers were separated. The aqueous phase was extracted with EtOAc (4×250 mL). The combined organic layer was washed with brine (2×100 mL), dried (Na2SO4), and filtered. The filtrate was concentrated under reduced pressure to afford 25.75 g (100%) of compound 2 as a tan solid that was used in subsequent reactions without any further purification. 1H NMR (300 MHz, DMSO-d6): δ 6.89 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.4 Hz, 2H), 7.66 (d, J=8.7 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 10.48 (s, 1H).

Provenance & Evidence