Acetic Acid → 3-bromo-2-phenyl-4H-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

To a round-bottom flask was added 2-phenyl-chromen-4-one (0.94 g, 4.23 mmol), acetic acid (40 mL) and N-bromosuccinimide (0.83 g, 4.65 mmol). The reaction mixture was heated to 100° C. using a hot oil bath with a water cooled reflux condenser, while stirring for 1 hour. The reaction mixture was cooled to RT and the solvents were removed in vacuo. The residue was suspended in ethyl acetate, washed with a saturated aqueous sodium hydrogen carbonate solution, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (10:1 hexane:EtOAc) to give a white solid (527 mg, 41%). 1H-NMR (400 MHz, CDCl3) δ 8.31 (d, 1H), 7.75 (d, 2H), 7.72 (dd, 1H), 7.45-7.56 (m, 5H).

Provenance & Evidence