Methanol → 4-Bromo-2-methoxy-3-methylbenzonitrile

Participants

Reaction Steps

Sodium (3.00 g, 130 mmol) was added in portions into 80 mL of methanol and the mixture was stirred for 20 min until the sodium was completely dissolved. Then 4-bromo-2-fluoro-3-methylbenzonitrile (8.00 g, 37.3 mmol) was added and the solution was refluxed for 4 hours before cooling down. The reaction mixture was poured into ice/water (300 mL) and the resulting precipitate was collected by filtration. The solid afforded was dried under reduced pressure at 40° C. to give 4-bromo-3-methyl-2-(methyloxy)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.39 (d, J=8.0 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H), 4.00 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence