2,6-Dimethylaniline → 4-Bromo-2,6-xylidine

Participants

Reaction Conditions

Reaction Steps

21.3 ml (66.1 g, 0.413 mol) of bromine were added dropwise, while vigorously stirring, over ca. 20 minutes to a solution of 50.0 g (0.413 mol) of 2,6-dimethylaniline in 1200 cm3 of glacial acetic acid. This mixture was stirred for 2 hours at 40° C. The precipitate formed was filtered off, washed with 50 ml of acetic acid, and dried in air. Then, this white solid was added to a solution of 100 g of sodium hydroxide in 600 ml of water. This mixture was stirred for 30 minutes. The crude product was extracted with 3×100 ml of dichloromethane. The combined organic fractions were dried over Na2SO4 and evaporated to dryness. Fractional distillation gave a yellow liquid, bp 82-85° C./1 mm Hg. Yield 61.7 g (75%).

Provenance & Evidence