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

Participants

Reaction Steps

To a solution of 5-bromo-2-fluorotoluene (15 g, 0.079 mole) in CCl4 (150 mL) was added NBS (14.2 g, 0.080 mole). The resulting reaction solution was heated under reflux with the starting material being completely consumed within 2 hr. CCl4 was removed under reduced pressure and the residue was diluted, dissolved in ether, washed with brine (3×), dried over MgSO4, and concentrated. Chromatography using hexane yielded 5-bromo-2-fluorobenzyl bromide. The product was immediately used for the reaction below.

Provenance & Evidence