Benzyl Bromide → 1-(Benzyloxy)-2-bromo-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-4-nitrophenol (Description 6; 14 g, 68.6 mmol), benzyl bromide (14.1 g, 82.4 mmol) and potassium carbonate (47.3 g, 0.343 mol) in dimethylformamide (100 ml) was heated at 60° C. for 3 hours. The mixture was cooled to room temperature and poured into a mixture of ethyl acetate and water. The organic phase was washed with water (3 times) and saturated brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallized from methanol to give the title compound (19 g). H NMR (250 MHz, CDCl3) δ 8.48 (1H, d, J 2.8 Hz), 8.18 (1H, dd, J 9.08 Hz, 2.8 Hz), 7.46−7.3 (5H, m), 7.0 (1H, d, J 9.2 Hz), and 5.27 (2H, s).

Provenance & Evidence