5-Tert-butyl-m-xylene → 1-(Bromomethyl)-3-tert-butyl-5-methylbenzene

Participants

Reaction Steps

5-tert-butyl-m-xylene (15g) was dissolved in carbon tetrachloride (80ml), N-bromosuccinimide (16.45g) and a catalytic amount of azoisobutyronitrile were added and the reaction was heated at reflux for 4h. The reaction was cooled and the mixture filtered to remove the succinimide. The solvent was removed in vacuo to afford a light brown oil. Purification was carried out by chromatography on silica gel (eluting silica with 100% petroleum ether, bp 60°-800° C.) to afford 3-t-butyl-5-methylbenzyl bromide as a clear oil (15.3g). 1H NMR (360MHz, CDCl3) d 1.31 (9H; s; t-Bu), 2.34 (3H; s; CH3), 4.47 (2H; s; CH2Br), 7.04 (1H; s; Ar H), 7.13 (1H; s; Ar H), 7.25 (1H; s; Ar H). m/z (CI+)=258 (M+NH4+).

Provenance & Evidence