Azobisisobutyronitrile → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

Participants

Reaction Steps

A solution of 4-bromo-3-fluorotoluene (11.34 g, 60 mmol), azobisisobutyronitrile (0.99 g, 6 mmol), and N-bromosuccinimide (11.75 g, 66 mmol) in carbon tetrachloride (60 ml) was heated to reflux for 3.5 h. The reaction mixture was cooled to room temperature and then filtered through Celite, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:hexane=0:100 to 100:0, gradient) to obtain the title compound (12.8 g, 80%) as a light yellow solid.

Provenance & Evidence