Dimethyl Sulfoxide → Benzene, 1-(1-methylethenyl)-4-(trifluoromethoxy)-

Temperature

80 °C

To a stirred suspension of 60% sodium hydride (1.96 g, 49 mmol) was added DMSO (20 ml) dropwise at 0° C. and the mixture was stirred at 80° C. for 30 minutes. After cooling the mixture to 0° C., a solution of methyltriphenylphosphonium bromide (17.5 g, 49 mmol) in DMSO (60 ml) was added dropwise at 0° C. and stirred at ambient temperature for 45 minutes. Then, to this mixture 1-[4-(trifluoromethoxy)phenyl]ethanone (5 g, 24.5 mmol) was added dropwise at ambient temperature and stirred at ambient temperature for 1 hour. The reaction was quenched with a small amount of acetone and diluted with hexane and water. The resulting precipitates were filtered and the organic layer was separated. After evaporation of the solvent, the residue was washed with hexane and concentrated in vacuo to afford 5.1 g (quant.) of the title compound as a colorless oil

1. temperatureAfter cooling the mixture to 0° C.
2. stirringstirred at ambient temperature for 45 minutes
3. stirringstirred at ambient temperature for 1 hour
4. customThe reaction was quenched with a small amount of acetone
5. additiondiluted with hexane and water
6. customThe resulting precipitates
7. filtrationwere filtered
8. customthe organic layer was separated
9. customAfter evaporation of the solvent
10. washthe residue was washed with hexane
11. concentrationconcentrated in vacuo

ORD record

ord-4da61a13f91b4cfa9ef03e4ba894c463

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915448B2