Azobisisobutyronitrile → 4-Cyano-3-fluorobenzyl bromide

Participants

Reaction Steps

To a solution of 4-cyano-3-fluorotoluene, as described above in Step C, (5.0 g, 37.0 mmol) in carbon tetrachloride (300 mL) was added N-bromosuccinimide (7.57 g, 42.6 mmol) and 2,2′-azobisisobutyronitrile (610 mg, 3.7 mmol). The reaction mixture was heated to reflux under argon for 24 hours, then cooled to room temperature, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with a gradient of hexane—4% to 7% EtOAc, to yield the titled product as a yellow solid.

Provenance & Evidence