Benzyl Bromide → HCID 67085084, compound

Participants

Reaction Steps

A mixture of 5-bromo-2-nitrophenol (10.4 g, 47.7 mmol), benzyl bromide (9.8 g, 57.2 mmol) and potassium carbonate (9.9 g, 71.5 mmol) was taken up in acetone (50 mL) and heated to reflux for 5 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 2-(benzyloxy)-4-bromo-1-nitrobenzene (14.19 g, 97%) as a light-yellow solid: 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=8.4 Hz, 1H), 7.32-7.48 (m, 5H), 7.30 (d, J=1.8 Hz, 1H), 7.19 (dd, J=8.7, 1.8 Hz, 1H), 5.23 (s, 2H).

Provenance & Evidence