N-bromobutanimide → 2-Bromo-1-(bromomethyl)-4-fluorobenzene

Participants

Reaction Steps

Combine 2-bromo-4-fluoro-1-methyl-benzene (15 g, 79.3 mmol), N-bromosuccinimide (18.08 g, 101.6 mmol), and 2,2-azobisisobutyronitrile (3.9 g, 23.8 mmol) in carbon tetrachloride (150 mL) in a round bottom flask fitted with a reflux condensor. Heat the mixture at reflux for 21 h. Cool the mixture and remove the solvent under reduced pressure. Suspend the crude mixture in DCM and wash with water. Wash the organics with aqueous saturated sodium chloride and dry over sodium sulfate. Filter and remove the solvent under reduced pressure to obtain the crude product. Purify by column chromatography (1% ethyl acetate in hexane→10% ethyl acetate in hexanes) to give the title compound as an oily white solid (18.5 g, 87%). GCMS m/z 268 [M]+.

Provenance & Evidence