Hydrogen Bromide → HCID 86708802, compound

Participants

Reaction Steps

4-Bromo-3-(difluoromethoxy)benzoic acid (6.65 mmol) was suspended in DCM (33 mL) and thionyl chloride (2.9 mL, 33 mmol) was added, followed by DMF (5 drops). After stirring at RT for 2 h, the reaction mixture was concentrated under reduced pressure. The crude residue was dissolved in DCM (17 mL) and treated with TMS-diazomethane (2.0 M in hexane, 8.3 mL, 16.6 mmol). After stirring at RT for 2 h, HBr (33% w/w in AcOH) (5.8 mL, 33 mmol) was added dropwise. After stirring for 1 h more at RT, the reaction mixture was concentrated under reduced pressure. The crude residue was diluted with EtOAc. The organic solution was washed with saturated aqueous NaHCO3 and brine, then dried over MgSO4, filtered and concentrated to afford 2-Bromo-1-(4-bromo-3-(difluoromethoxy)phenyl)ethanone (yield undetermined, material carried on crude assuming total conversion).

Provenance & Evidence