Triethylamine → 2-Bromo-N-tert-butyl-N-phenyl-acetamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7.91 g (53.0 mmol) tert-Butyl-phenyl-amine (Biehl, Smith, Reeves, J. Org. Chem., 1971, 13, 1842) and 5.36 g (58.3 mmol, 1.1 equiv) Et3N in 60 mL DCM is added 11.77 g (58.3 mmol, 1.1 equiv) Bromoacetyl bromide in 40 mL DCM dropwise over 45 minutes at 0° C. The reaction mixture is stirred 3 h at 0° C., diluted with 200 mL DCM, washed with 1N HCl (2×150 mL), dried (MgSO4), and concentrated in vacuo. The crude product is filtered through a pad of 15 g silica gel eluted with 300 mL DCM. The filtrate is concentrated in vacuo to give 12.40 g (45.9 mmol) of 2-Bromo-N-tert-butyl-N-phenyl-acetamide as an amber oil: 1H NMR (CDCl3, 300 MHz) δ7.45-7.21 (m, 12H), 7.08 (t, 1H), 6.90 (m, 1H), 4.30 (d, 1H, J=16.4), 3.85 (d, 1H, J=16.6), 3.59 (d, 1H, J=12.0), 3.49 (d, 1H, J=11.9), 1.43 (s, 9H); TLC Rf =0.24 (EtOAc/Hexanes, 1:1).

Provenance & Evidence