Triethylamine → 2-Bromo-N-isopropyl-N-p-tolyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6.07 g (40.7 mmol) Isopropyl-p-tolyl-amine, prepared as in Part A, and 4.12 g (40.7 mmol, 1 equiv) Et3N in 50 mL DCM is added 8.22 g (40.7 mmol, 1 equiv) Bromoacetyl bromide in 25 mL DCM dropwise over 30 minutes at 0° C. The reaction mixture is stirred 1 h at 0° C. followed by warming to ambient temperature and stirring 18 h. The reaction mixture is washed with 1N HCl (3×50 mL), dried (MgSO4), filtered through a pad of 20 g silica gel eluted with 400 mL DCM, and concentrated in vacuo to give 9.39 g (34.5 mmol) of 2-Bromo-N-isopropyl-N-p-tolyl-acetamide as an amber oil: 1H NMR (CDCl3, 300 MHz) δ7.25 (d, 2H, J=8.1), 7.09 (d, 2H, J=8.3), 4.96 (m, 1H), 3.55 (s, 2H), 2.42 (s, 3H), 1.07 (d, 6H, J=6.8); TLC Rf =0.23 (EtOAc/Hexanes, 1:9).

Provenance & Evidence