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

Temperature

100 °C

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).

1. customthe bulk of the tetrahydrofuran was removed in vacuo
2. additionDichlorobis(triphenylphosphine)palladium(II) (0.23 g) was added to the residual N,N-dimethylformamide solution, which
3. temperaturecooled to room temperature
4. additionThe resulting mixture was poured into water (100 mL)
5. extractionextracted with diethyl ether (100 mL×1)
6. washThe organic layer was washed with water and brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customto provide a residue
10. customThe residue was purified by column chromatography on silica gel
11. washeluted with hexane

ORD record

ord-d33ae471ca9b4346923646786bfc8216

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947715B2