4-Hydroxybenzaldehyde → 4-(3-Bromopropoxy)benzaldehyde

Participants

Reaction Steps

A solution of 4-hydroxybenzaldehyde (3.7 g, 30 mmol) in DMF (10 ml) was added cautiously to a stirred solution of sodium hydride (60% in oil, 1.44 g) in DMF (80 ml). After 30 min., 1,3-dibromopropane (9.2 ml, 90 mmol) in DMF (10 ml) was added dropwise, the mixture stirred for 16 h, poured into water, extracted twice with ethyl acetate, and the combined extracts washed with water and saturated aqueous sodium chloride, dried over sodium sulphate and evaporated. The residue was purified by flash chromatography on silica, eluting with 25% diethyl ether in hexane, to afford 4-(3-bromopropyloxy)benzaldehyde (3.85 g). M+ 205; 360 MHz 1H n.m.r (CDCl3) 7.85 (2H, d, J 7.0 Hz), 7.01 (2H, d, J 7.0 Hz), 4.20 (2H, t, J 5.8 Hz), 3.62 (2H, t, J 6.4 Hz), 2.36 (2H, pentet, J 6.1 Hz).

Provenance & Evidence