1-Bromo-3-chloropropane → 1-(3-Chloropropoxy)-4-iodobenzene

Participants

Reaction Steps

A mixture of p-iodophenol (20 g, 91 mmol), potassium carbonate (25.2 g, 182 mmol) and 1-bromo-3-chloropropane (commercially available, for example, from Aldrich) (18 g, 114 mmol) in anhydrous 2-butanone (300 ml) was heated at reflux for 72 h, cooled to room temperature, filtered and evaporated to dryness. The resulting residue was purified by SPE filtration (70 g silica cartridge, eluting with 20:1 cyclohexane-ethyl acetate) to afford the title compound (24.9 g); 1H NMR (CDCl3) δ 7.5 (2H, d), 6.7 (2H, d), 4.1 (2H, t), 3.8 (2H, t), 2.2 (2H, q).

Provenance & Evidence