Azobisisobutyronitrile → Ethyl 2-(4-bromomethylphenoxy)phenylacetate

Participants

Reaction Steps

N-Bromosuccinimide (6.64 g) and azo(bisisobutyronitrile) (400 mg) were added to a solution of compound (B) (10.1 g) in carbon tetrachloride (100 ml). The mixture was heated under reflux for 20 hours and then cooled to ambient temperature. Insoluble material was removed by filtration and the filtrate was concentrated. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:19 v/v), to give ethyl 2-(4-bromomethylphenoxy)phenylacetate (C) (5.9 g), as an oil; NMR (d6 -DMSO): 1.15(t, 3H), 4.1(q, 2H), 4.65(s, 2H), 6.0(s, 1H), 6.95(d, 2H), 7.3-7.5(m, 5H), 7.5-7.6(m, 2H).

Provenance & Evidence