N-Methyl-4-nitroaniline → 2-bromo-N-methyl-N-(4-nitrophenyl)acetamide

Participants

Reaction Steps

A mixture of 2.00 g (13.2 mmol) of N-methyl-4-nitroaniline and 1.46 g (14.5 mmol) of Et3N in 20 mL of CH2Cl2 at O° C. under N2 is treated with a solution of 5.33 g (26.4 mmol) of bromoacetyl bromide in 4 mL of CH2Cl2. After 3.5 h, the reaction is poured into ice water and extracted with CH2Cl2. The extract is treated with Darco, dried (MgSO4) and evaporated. The residue is filtered through Magnesol (CHCl3), evaporated and dried in vacuo to give 3.57 g (100%) of yellow solid. 1H NMR (DMSO-d6) δ 8.27 (d, 2H, J=7.47 Hz), 7.66 (d, 2H, J=7.47 Hz), 4.06 (s, 2H), 3.28 (s, 3H); MS (ESI) m/z 273.0 (M+1).

Provenance & Evidence