3-Methoxytoluene → 3-Methoxybenzyl bromide

Participants

Reaction Steps

To a solution of 122 g (1.0 mol) of 1-methoxy-3-methylbenzene in 900 ml of CCl4, 178 g (1.0 mol) of NBS and 1.0 g of (PhCO2)2 were added at room temperature. This mixture was refluxed for 3 h, cooled to room temperature, and the formed succinimide was filtered off. Succinimide was additionally washed by 2×150 ml of CCl4. The combined filtrate was evaporated to dryness, and the residue was distilled in vacuum, b.p. 112-125° C./8 mm Hg. This procedure gave 152.5 g of 1-(bromomethyl)-3-methoxybenzene contaminated with ca. 25% of the isomeric product, i.e. 1-bromo-4-methoxy-2-methylbenzene.

Provenance & Evidence