Triethylamine → 2-bromo-N-isopropyl-N-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-isopropylaniline (21.58 g, 180 mmol) in CH2Cl2 (350 mL) was added triethylamine (26.7 mL, 190 mmol). The solution was cooled to 0° C. and bromoacetyl bromide (14.0 mL, 160 mmol) was added slowly over 1 hour. The reaction was warmed to room temperature and was stirred for 24 hours. The reaction was diluted with 5% aqueous HCl. The organic solution was washed with 5% aqueous HCl (2×), aqueous NaHCO3 (1×), and brine (1×). The organic solution was filtered through a silica gel pad, eluting with CH2Cl2. Recrystallization from hexanes (60 mL) provided 22.47 g of 2-bromo-N-isopropyl-N-phenyl-acetamide. 1H NMR (CD2Cl2) δ 7.45 (m, 3H), 7.21 (m, 2H), 4.89 (m, 1H), 3.52 (s, 2H), 1.05 (d, 6H); MS 256.2 (M+1).

Provenance & Evidence