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

Participants

Reaction Steps

A mixture of 4-bromo-2-nitro-phenol (5.05 g, 23.16 mmol), benzyl bromide (4.12 mL, 34.73 mmol) and K2CO3 (9.60 g, 69.48 mmol) in acetone (200 mL) were stirred, and refluxed for 3 hours. The solution was filtered, dried with silica gel powder (20 g), and separated by flash chromatography eluting with 5% ethyl acetate in hexanes (1 L) and then with 20% ethyl acetate in hexanes (1 L) to give the title compound (6.84 g, 96%). MS (DCI) m/z 326.90 (M+NH4)+; 1H NMR (500 MHz, CD2Cl2) δ ppm 5.21 (s, 2 H) 7.06 (d, J=9.05 Hz, 1 H) 7.33–7.46 (m, 5 H) 7.63 (dd, J=8.73, 2.50 Hz, 1 H) 7.97 (d, J=2.50 Hz, 1 H).

Provenance & Evidence