Triethylsilane → N-[5-Chloro-4-(2-chloro-ethyl)-2-methyl-phenyl]-acetamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamide (10 g, 38.44 mmol) in trifluoroacetic acid (100 mL) at <20° C. was added portionwise, triethylsilane (15.35 mL, 96.1 mmol). The reaction was heated to 60° C. and stirred overnight. The reaction was cooled to rt and poured over ice/H2O and stirred for 30 min as a grey precipitate formed. The precipitate was collected by filtration and dried in vacuo overnight to give desired product (8.35 g, 33.92 mmol). Yield=88%; MS (APCI): 246 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.05 (s, 1H), 6.93 (bs, 1H, NH), 3.69 (t, J=7.26 Hz, 2H), 3.10 (t, J=7.26 Hz, 2H), 2.20 (d, J=4.48 Hz, 3H).

Provenance & Evidence