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

Participants

Reaction Steps

To a solution of 4-bromo-2-nitrophenol (5.2 g, 23.8 mmol) in acetone (100 ml) was added potassium carbonate (9.0 g, 65.1 mmol) followed by benzyl bromide (2.6 ml, 21.8 mmol). The resulting mixture was stirred at room temperature for 30 minutes and then heated to reflux overnight. The solids were then removed by filtration, washing with acetone, and the filtrate reduced in vacuo. The residue was dissolved in ethyl acetate and washed with 2M aqueous sodium hydroxide solution (×3) and then brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and reduced in vacuo to afford 4-bromo-2-nitro-1-[phenylmethyl)oxy]benzene (6 g), 92% yield. 1H NMR (500 MHz, CDCl3): δ 5.26 (s, 2H), 7.05 (d, J=8.9 Hz, 1H), 7.42 (m, 5H), 7.63 (dd, J=2.5 Hz, 1H), 8.01 (d, J=2.45 Hz, 1H). 13C NMR (500 MHz, CDCl3): δ 71.6, 112.4, 116.9, 127.1, 128.5, 128.6, 128.9, 135.2, 136.9, 140.7, 151.2.

Provenance & Evidence