Diethyl Ether → HCID 15278694, compound

Participants

Reaction Conditions

Reaction Steps

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+).

Provenance & Evidence