5-Bromo-2,3-dichlorotoluene → HCID 66865196, compound

Temperature

100 °C

To 1M solution of 1-(trifluoromethyl)ethenyl zinc bromide in tetrahydrofuran (see J. Org. Chem. 1991, 56, 7336 for preparation) (19 mL) was added a solution of 5-bromo-2,3-dichlorotoluene (2.2 g) in N,N-dimethylformamide (10 mL), then tetrahydrofuran was distilled off under reduced pressure. Dichlorobis(triphenylphosphine)palladium(II) (0.26 g) was added to the residual N,N-dimethylformamide solution, which was stirred at 100° C. for 3.5 hours under nitrogen atmosphere and then cooled to room temperature. To the resulting mixture was added tetrahydrofuran-hexane 2:5 mixture (200 mL) and filtered, and the filtrate was washed with water (100 mL) 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 (2.3 g).

1. distillationtetrahydrofuran was distilled off under reduced pressure
2. additionDichlorobis(triphenylphosphine)palladium(II) (0.26 g) was added to the residual N,N-dimethylformamide solution, which
3. temperaturecooled to room temperature
4. additionTo the resulting mixture was added tetrahydrofuran-hexane 2:5 mixture (200 mL)
5. filtrationfiltered
6. washthe filtrate was washed with water (100 mL) 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-bc0bd53f42674413aa1656d6e7b94e30

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242283B2