Ethanol → HCID 118113450, compound

To a suspension in acetonitrile (60.0 mL) of the compound (2.08 g) obtained in step (3) above and sodium nitrite (2.10 g), conc. sulfuric acid (6.00 mL) was added at 0° C. over a period of 15 minutes. After stirring the mixture at that temperature for an hour, ethanol (24.0 mL) was added. After being stirred at 100° C. for two hours, the reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into iced water and two extractions were conducted with chloroform. The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure and the residue was purified twice by NH silica gel column chromatography (with n-hexane only) to give 2-cyclobutyl-4-iodo-1-(trifluoromethyl)benzene as a colorless oil (1.25 g).

1. stirringAfter being stirred at 100° C. for two hours
2. stirringthe reaction mixture was stirred overnight at room temperature
3. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate
4. dry with materialdried over anhydrous magnesium sulfate
5. customAfter removing the
6. filtrationdesiccant by filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customthe residue was purified twice by NH silica gel column chromatography (with n-hexane only)

ORD record

ord-27eeaf4dabc849cabd1763c97d9f8bc7

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422240B2