Bromine → HCID 89954219, compound

{3-(4,4-Difluorocyclohexyl)-1-(1-trifluoromethylcyclopropyl)prop-1-enyloxy}triethylsilane (3.00 g, 7.53 mmol) obtained in step 4 was dissolved in dichloromethane (30 mL). Under ice-cooled condition, a dichloromethane solution (10 mL) of bromine (1.32 g, 8.28 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was extracted with hexane after adding a saturated sodium hydrogen carbonate aqueous solution, and a sodium thiosulfate aqueous solution. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20) to give 2-bromo-3-(4,4-difluorocyclohexyl)-1-(1-trifluoromethylcyclopropyl)propan-1-one (2.69 g, yield 98%).

1. temperatureUnder ice-cooled condition
2. extractionThe reaction mixture was extracted with hexane
3. additionafter adding a saturated sodium hydrogen carbonate aqueous solution
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was then evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→80/20)

ORD record

ord-0555b317194c47d38a9cd09beaf74cfe

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000186B2