Allyl bromide → 1-(3-Bromopropyl)-3-methoxybenzene

Participants

Reaction Steps

Allyl bromide (25 mL, 0.28 mmol) was added to a solution of 3-(3-methoxyphenyl)propanol (8.8 g, 0.053 mol), N,N′-carbonyldiimidazole (9.6 g, 0.0605 mol) and CH3CN (45 mL) at room temperature. After 1.5 hr at rt and 1.5 hr at reflux, the reaction mixture was cooled, partitioned between EtOAc (250 mL) and H2O (300 mL), the organic layer washed with H2O (300mL), 5% HCl (200 mL), dilute NaHCO3 solution (200 mL), brine (300 mL), and dried (Na2SO4). Filtration and concentration to dryness gave the title compound.

Provenance & Evidence