N-bromobutanimide → 3-Bromo-6-fluoro-2-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of 2-fluoro-6-methylbenzonitrile (5.0 g, 37 mmol) in 100 mL of concentrated H2SO4 was added NBS (6.93 g, 38.9 mmol). Then the mixture was stirred at 0° C. for 3 hrs and poured into ice-water (1 L). The solution was extracted three times with EtOAc (200 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel flash chromatography to give 3-bromo-6-fluoro-2-methylbenzonitrile.

Provenance & Evidence