Bromine → 1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Participants

Reaction Steps

4-Benzyloxyacetophenone (56.57 g, 250 mmol) was dissoved in 1350 ml of methanol, with warming, and bromine (15.5 ml, 300 mmol) was added dropwise as a solution in 150 ml of methanol. After stirring for 3 hours the methanol was evaporated and the residue was suspended in 200 ml of 1 M hydrochloric acid and stirred for 10 minutes. The organic material was extracted into dichloromethane (1×500 ml, and 1×200 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to an off-white solid, which was recrystalized from hot ethanol and water, to afford 69.39 g (91%) of 4-benzyloxyphenacylbromide. M.p. 85-88° C. MS(GC): m/z 306 (M+1). 1H-NMR (CDCl3, 200 MHz) δ: 4.39 (s, 2H); 5.13 (s, 2H); 7.03 (d, 2H); 7.32-7.46 (m, 5H); 7.98 (d, 2H).

Provenance & Evidence