Carbon Tetrachloride → 3-Chloro-5-methoxybenzyl bromide

Participants

Reaction Steps

To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CCl4 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with 1N HCl (2 L), satd NaHCO3 (2 L) and brine (2 L), dried over MgSO4, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3-chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400 MHz, CDCl3): δ 7.30-7.34 (d, 1H), 6.95 (s, 1H), 6.91-6.93 (d, 1H), 4.45 (s, 2H), 3.92 (s, 3H).

Provenance & Evidence