Trifluoroacetic acid → 3-Bromo-6-fluoro-2-methylbenzonitrile

Participants

Reaction Steps

NBS (265 g, 1490 mmol) was added portion wise to a stirred, cooled room temperature mixture of 2-Fluoro-6-methylbenzonitrile (191.8 g, 1419 mmol) in TFA (553 mL, 8500 mmol) and then the mixture was heated at reflux for 48 hours. The reaction was poured into 1 L of ice, diluted with 700 mL 30% EtOAc/Hexanes, and agitated. The aqueous layer was cut, and the organic layers were washed with 1N NaOH twice and with water. The organic layers were dried over Na2SO4, concentrated, and then stored in a −10° C. freezer overnight. The resulting crystals were filtered and washed with 5% EtOAc/Hexanes to yield the title product.

Provenance & Evidence