N-(4-Methoxyphenyl)Acetamide → N-(3-bromo-4-methoxyphenyl)acetamide

Participants

Reaction Steps

To a solution of 10.0 g (60.5 mmol) of 4-acetaminoanisole (5) in 80 mL of acetic acid, was added dropwise 11.6 g (72.7 mmol) of bromine and maintaining internal temperature of the reaction below 50° C. After stirring for 1 h, the reaction mixture was poured into 400 mL of ice-water containing 1.2 g of NaHSO3. The mixture was stirred until yellow-red color disappeared and left at room temperature for overnight. The solid (product) was filtered, dried under vacuum at 70° C., and crystallized from ethanol to give 10.19 g (69% yield). 1H NMR (CDCl3) δ 7.67 (d, J=2.5 Hz, 1 H), 7.44 (dd, J=9, 2.5 Hz, 1 H), 7.1 (bs, 1 H, NH), 6.85 (d, J=9 Hz, 1 H), 3.87 (s, 3 H, OMe), 2.16 (s, 3 H, CH3).

Provenance & Evidence