Diethyl Ether → HCID 15278694, compound

Temperature

84 °C

A 100 mL pressure bottle was charged with 1-acetyl-3-chloro-2-[[(trifluoromethyl)sulfonyl]oxy]benzene (2.41 mmol, 0.73 g), Pd(OAc)2 (0.2 mmol, 47 mg) and dppp (0.2 mmol, 87 mg). Then, the flask was closed with a septum and evacuated three times with argon. Then, acetonitrile (96 mL), triethylamine (188.7 mmol, 19.0 g, 26.25 mL) and water (19.1 mL) were added successively by the aid of syringe. Then, the rubber septum was replaced with teflon lined cap connected to a carbon monoxide source. The flask was now pressurized with carbon monoxide (40 psi) and the excess pressure was released. This process was repeated three times and finally the mixture was stirred for 5 min under 40 psi carbon monoxide pressure. The flask was then disconnected from the carbon monoxide cylinder and immersed in a preheated oil bath (83-85° C.) and stirred for 3 hr. The reaction mixture was cooled to room temperature and the pressure was released and the mixture was diluted with ether (200 mL) and 1.0N NaOH (20 mL). The acid was extracted into water (2×100 mL). The combined water extracts were neutralized with 1.0N HCl and again the acid was extracted into dichloromethane (3×100 mL). The combined dichloromethane extracts were washed with brine solution and dried over MgSO4. Filtration of the drying agent and removal of solvent under vacuum gave a crude residue which was recrystallized from dichloromethane (˜10 mL) and hexane (˜8 mL) and storage in the refrigerator overnight. The precipitated solid was collected by filtration and dried under high vacuum to afford 330 mg (69%) of a colorless solid: mp 128-129° C. HR MS: Obs. mass, 198.0090. Calcd. mass, 198.0084 (M+).

1. customThen, the flask was closed with a septum
2. customevacuated three times with argon
3. customlined cap
4. customimmersed in a preheated oil bath
5. temperatureThe reaction mixture was cooled to room temperature
6. extractionThe acid was extracted into water (2×100 mL)
7. extractionagain the acid was extracted into dichloromethane (3×100 mL)
8. washThe combined dichloromethane extracts were washed with brine solution
9. dry with materialdried over MgSO4
10. filtrationFiltration of the drying agent and removal of solvent under vacuum
11. customgave a crude residue which
12. customwas recrystallized from dichloromethane (˜10 mL) and hexane (˜8 mL) and storage in the refrigerator overnight
13. filtrationThe precipitated solid was collected by filtration
14. customdried under high vacuum

ORD record

ord-b78670faffff49499674c2c8e342b36d

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06229011B1