N-bromobutanimide → 4-Bromo-1-(bromomethyl)-2-chlorobenzene

Participants

Reaction Steps

4-Bromo-2-chloro-1-methylbenzene (CAS 89794-02-5, 30 g, 0.15 mol) and N-bromosuccinimide (26 g, 0.15 mol) were mixed in CCl4 (300 mL). Azobis(2-methylpropionitrile) (˜0.3 g) was added in portions under vigorous stirring and refluxing. The mixture was refluxed for 30 min and cooled. The precipitate was filtered off and discarded. The filtrate was evaporated. The residue was distilled at 1 mmHg, bp 75° C. to give the title compound (28 g, 65%). 1H NMR data (CDCl3): δ 7.57 (d, J=1.9 Hz, 1H ArH), 7.39 (dd, 1H, J1=1.9 Hz, J2=8.1 Hz, ArH), 7.31 (d, 1H, J=1.9 Hz, ArH), 4.53 (s, 2H, ArCH2).

Provenance & Evidence