Benzyl Bromide → HCID 59395018, compound

Participants

Reaction Steps

To a solution of 4-bromo-5-nitro-2-cyclopentylphenol (21.7 g, 75.9 mmol) and Cs2CO3 (29.7 g, 91.1 mmol) in DMF (190 mL) was added benzylbromide (14.6 g, 10.1 mL, 83.5 mmol) dropwise at room temperature. The reaction was stirred for 16 h. The reaction was diluted with water and extracted with ethyl acetate (3×100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (ethyl acetate/hexane gradient) provided 1-(benzyloxy)-4-bromo-2-cyclopentyl-5-nitrobenzene (28.0 g, 98% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 7.56 (d, J=10.6 Hz, 2H), 7.51-7.37 (m, 5H), 5.14 (s, 2H), 3.44-3.35 (m, 1H), 2.12-2.05 (m, 2H), 1.86-1.55 (m, 6H).

Provenance & Evidence