Methyl iodide → 5-Bromo-2-chloro-4-methoxybenzonitrile

Participants

Reaction Steps

To a solution of 5-bromo-2-chloro-4-hydroxybenzonitrile (7.0 g, 30.11 mmol) in DMF (70 mL) was added cesium carbonate (19.62 g, 60.22 mmol, GLR Scientific) and MeI (3.74 mL, 60.22 mmol, Spectrochem). The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with ice cold water (500 mL) and extracted with ethyl acetate (2×500 mL). The combined organic layer was washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography (silica gel 100-200 mesh and 0-4% EtOAc in hexane) to obtain 5-bromo-2-chloro-4-methoxybenzonitrile (5.5 g, 74.1%) as white solid. m/z (ESI) N/A (no ionization observed).

Provenance & Evidence