Carbon tetrabromide → Ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoate

Participants

Reaction Steps

To a stirred solution of ethyl 2-[4-(2-hydroxyethyl)-phenoxy]-2-methylpropionate (474 mg) and triphenylphosphine (591 mg) in dichloromethane (10 ml) was added carbon tetrabromide (748 mg) under ice-cooling, and the mixture was stirred for 40 minutes. Rough purification of the reaction mixture by flash column chromatography on silica gel (eluent: diethylether) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=10/1) gave ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropionate (500 mg). 1H-NMR (CDCl3) δ ppm: 1.25 (3H, t, J=7.1 Hz), 1.59 (6H, s), 3.09 (2H, t, J=7.8 Hz), 3.52 (2H, t, J=7.8 Hz), 4.23 (2H, q, J=7.1 Hz) 6.79 (2H, d, J=8.7 Hz), 7.07 (2H, d, J=8.7 Hz)

Provenance & Evidence