Water → 2-Bromo-3-nitroanisole

Participants

Reaction Steps

To a solution of 2-bromo-3-nitro-phenol synthesized above (11.5 mmol, 1.0 eq.) in DMF at room temperature was added cesium carbonate (13.8 mmol, 1.2 eq.), followed by iodomethane (33.7 mmol, 2.9 eq.), and the resultant mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into water, stirred for 2 hours, filtered, the cake washed with two portions of water, and the resultant solid dried to afford 2-bromo-3-nitro-anisole (I-9, X═Br, R1═CH3) as a pale orange solid. Yield: 97%; 1H NMR (400 MHz; CDCl3): 3.97 (s, 3H), 7.07 (dd, J=8.4, 1.2 Hz, 1H), 7.32 (dd, J=8.0, 1.6 Hz, 1H), 7.40 (t, J=8.0 Hz, 1H) ppm.

Provenance & Evidence