Dimethylformamide → 2-(4-bromophenyl)-N-methylacetamide

Participants

Reaction Steps

To a solution of 4-bromophenyl acetic acid (50 g, 233 mmol) in SOCl2 (170 mL, 2.32 mol) was added DMF (2 mL, 26 mmol). After stirred at this temperature for 1 h, the excess SOCl2 was removed under reduced pressure. The residue was dissolved in CH2Cl2 (300 mL), and the resulting solution was added to a cooled (0° C.) solution of CH3NH2 (90 mL, 40 wt % in H2O, 1.03 mol) in THF (200 mL) dropwise. After the addition was complete, the solution was further stirred at 0° C. for 15 min. Water (400 mL) was added to the reaction solution, and organic layer separated. The aqueous layer was extracted with CH2Cl2 (200 mL). The organic layers were combined, washed with brine (500 mL), dried and concentrated to give 4-bromophenyl-N-methyl acetamide (54 g, quant.) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.48 (d, J=8.9 Hz, 2H), 7.15 (d, J=8.9 Hz, 2H), 3.51 (s, 2H), 2.77 (s, 3H); ESI-MS m/z 228 [M+H]+.

Provenance & Evidence