Hydrochloric Acid → 4-Bromo-4'-methoxybenzophenone

Participants

Reaction Steps

To a cooled (ice bath, 5° C.) mixture of 4-bromobenzoyl chloride (25.0 g, 0.114 mol) and anisole (15.5 g, 0.143 mol, 1.25 eq) in CH2Cl2 (500 mL) was added AlCl3 (19.0 g, 0.143 mol, 1.25 eq) portion-wise over a period of 20 minutes with stirring under a nitrogen atmosphere. The resulting reaction mixture was allowed to stir between 5° C. and 20° C. for 3 h. The reaction mixture was poured slowly into 20% aqueous HCl (500 mL), stirred for 15 min, and layers were separated. The aqueous layer was further extracted with CH2Cl2 (3×250 mL). The combined organic layer was washed with water (200 mL), brine (200 mL) dried (Na2SO4), filtered, and concentrated under reduced pressure to afford 33.48 g (100%) of compound 1 as a white solid. 1H NMR (300 MHz, CDCl3): δ 3.91 (s, 3H), 6.99 (d, J=8.7 Hz, 2H), 7.65 (s, 4H), 7.82 (d, J=8.7 Hz, 2H).

Provenance & Evidence