5-Bromo-1,3-dichloro-2-(difluoromethoxy)benzene → HCID 86631570, compound

Participants

Reaction Conditions

Reaction Steps

To 1M solution of 1-(trifluoromethyl)ethenyl zinc bromide in tetrahydrofuran (see J. Org. Chem. 1991, 56, 7336 for preparation) (21 mL) was added a solution of 4-bromo-2,6-dichloro-1-(difluoromethoxy)benzene (2.4 g) in N,N-dimethylformamide (12 mL), then the bulk of the tetrahydrofuran was removed in vacuo. Dichlorobis(triphenylphosphine)palladium(II) (0.23 g) was added to the residual N,N-dimethylformamide solution, which was stirred at 100° C. for 3 hours under nitrogen atmosphere and then cooled to room temperature. The resulting mixture was poured into water (100 mL) and extracted with diethyl ether (100 mL×1). The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by column chromatography on silica gel eluted with hexane to afford the title compound as a brown oil (1.8 g).

Provenance & Evidence