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

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-nitro-phenol (Aldrich, 2.18 g, 10 mmol) was treated with K2CO3 (Aldrich, 2.76 g, 20 mmol) in DMF (Aldrich, 100 mL) at ambient temperature for 20 min. Benzyl chloride (Aldrich, 1.52 g, 12 mmol) was added. The mixture was stirred at 100° C. for 6 h. It was then poured into ice/water (200 mL) and stirred at ambient temperature for 10 hours. The white solid was filtered and dried to give the title compound (3.0 g, yield, 100%). 1H NMR (300 MHz, CDCl3) δ 5.23 (s, 2 H), 7.01 (d, J=9.2 Hz, 1 H), 7.31-7.49 (m, 5 H), 7.58 (dd, J=9.0, 2.5 Hz, 1 H), 7.98 (d, J=2.7 Hz, 1 H) ppm. MS (DCl/NH3): 325 (M+H)+, 327 (M+H)+.

Provenance & Evidence