Bromine → 4-Acetamido-3-bromo-2,6-dimethylanisole

Participants

Reaction Steps

4-Acetamido-2,6-dimethylanisole (7, 8.6 g, 44.3 mmol) and acetic acid (30 mL) were placed in a round-bottom flask under an argon atmosphere. Bromine (2.7 mL, 44.3 mmol) was added dropwise to the solution, after which the reaction mixture was stirred at room temperature for about 3 h, and then concentrated. The residue was diluted with methylene chloride and carefully washed sequentially with saturated aq. sodium bicarbonate and brine, and dried (MgSO4). Removal of solvents gave a brown-colored solid which was recrystallized from methylene chloride-hexanes to yield 4-acetamido-3-bromo-2,6-dimethylanisole (10.3 g, 85% yield) as an off-white solid, mp 152°-153° C. Spectral data: 1H NMR: δ 2.18 (s, 3H), 2.24 (s, 3H), 2.35 (s, 3H), 3.66 (s, 3H), 7.55 (br s, 1H), 7.9 (s, 1H); 13C NMR: δ 16.1, 16.8, 24.6, 60.1, 114.5, 122.0, 130.5, 131.3, 131.5, 153.6, 168.1; CI-HRMS: calcd. for C11H15BrNO2 (M+H+) 272.0286, fnd. 272.0284.

Provenance & Evidence