1,1,2,2-tetrafluoro-2-phenylsulfanylethanesulfonyl fluoride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Added to a solution of 1,2-dichloroethane (20 ml), containing the PhSCF2CF2SO2F (2.09 g, 7.2 mmol) obtained according to the method from example 3, was freshly distilled benzylamine (4 ml, 37 mmol). The mixture was stirred and heated at 50° C. for 20 h until the disappearance of PhSCF2CF2SO2F (monitored by TLC and 19F NMR/CDCl3). After returning to ambient temperature, an aqueous solution of HCl (10%) was added to the reaction medium. The aqueous and organic phases were separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined and dried over MgSO4. After filtration and evaporation of the solvents, the residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1). The sulfonamide product was obtained in the form of a white solid (2.1 g, 77%). obtained After returning to ambient temperature The aqueous and organic phases were separated the aqueous phase was extracted with dichloromethane dried over MgSO4 After filtration and evaporation of the solvents the residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of sulfur dioxide was prepared by bubbling sulfur dioxide (1.02 g, 16 mmol) in a solution of anhydrous acetonitrile (20 ml) at ambient temperature. This solution was added to PhSCF2CF2SiMe3 (8 mmol, prepared according to the procedure from example 2) and stirred at ambient temperature under an inert atmosphere. Anhydrous CsF (1.4 g, 9 mmol) was then added to the reaction mixture, which was stirred at ambient temperature overnight. The reaction was monitored by TLC and by 19F NMR (CDCl3) until the disappearance of PhSCF2CF2SiMe3. F-TEDA (2.9 g, 8.2 mmol) was added to the mixture, which was stirred for 1 h at ambient temperature. The mixture was concentrated and the solid residue washed with ethyl ether (10×50 ml). The filtrate was evaporated and the product purified by bulb-to-bulb distillation. The product 2-(phenylsulfanyl)-1,1,2,2-tetrafluoroethane-sulfonyl fluoride was obtained in the form of a colorless liquid (1.86 g, 79%). prepared was stirred at ambient temperature overnight was stirred for 1 h at ambient temperature The mixture was concentrated the solid residue washed with ethyl ether (10×50 ml) The filtrate was evaporated the product purified by bulb-to-bulb distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of sulfur dioxide was prepared by bubbling sulfur dioxide (1.02 g, 16 mmol) in a solution of anhydrous acetonitrile (20 ml) at ambient temperature. This solution was added to PhSCF2CF2SiMe3 (8 mmol, prepared according to the procedure from example 2) and stirred at ambient temperature under an inert atmosphere. Anhydrous CsF (1.4 g, 9 mmol) was then added to the reaction mixture, which was stirred at ambient temperature overnight. The reaction was monitored by TLC and by 19F NMR (CDCl3) until the disappearance of PhSCF2CF2SiMe3. F-TEDA (2.9 g, 8.2 mmol) was added to the mixture, which was stirred for 1 h at ambient temperature. The mixture was concentrated and the solid residue washed with ethyl ether (10×50 ml). The filtrate was evaporated and the product purified by bulb-to-bulb distillation. The product 2-(phenylsulfanyl)-1,1,2,2-tetrafluoroethane-sulfonyl fluoride was obtained in the form of a colorless liquid (1.86 g, 79%). prepared was stirred at ambient temperature overnight was stirred for 1 h at ambient temperature The mixture was concentrated the solid residue washed with ethyl ether (10×50 ml) The filtrate was evaporated the product purified by bulb-to-bulb distillation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Added to a solution of 1,2-dichloroethane (20 ml), containing the PhSCF2CF2SO2F (2.09 g, 7.2 mmol) obtained according to the method from example 3, was freshly distilled benzylamine (4 ml, 37 mmol). The mixture was stirred and heated at 50° C. for 20 h until the disappearance of PhSCF2CF2SO2F (monitored by TLC and 19F NMR/CDCl3). After returning to ambient temperature, an aqueous solution of HCl (10%) was added to the reaction medium. The aqueous and organic phases were separated and the aqueous phase was extracted with dichloromethane. The organic phases were combined and dried over MgSO4. After filtration and evaporation of the solvents, the residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1). The sulfonamide product was obtained in the form of a white solid (2.1 g, 77%). obtained After returning to ambient temperature The aqueous and organic phases were separated the aqueous phase was extracted with dichloromethane dried over MgSO4 After filtration and evaporation of the solvents the residue was purified by chromatography over silica gel (pentane to pentane/AcOEt:4/1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of sulfur dioxide was prepared by bubbling sulfur dioxide (1.02 g, 16 mmol) in a solution of anhydrous acetonitrile (20 ml) at ambient temperature. This solution was added to PhSCF2CF2SiMe3 (8 mmol, prepared according to the procedure from example 2) and stirred at ambient temperature under an inert atmosphere. Anhydrous CsF (1.4 g, 9 mmol) was then added to the reaction mixture, which was stirred at ambient temperature overnight. The reaction was monitored by TLC and by 19F NMR (CDCl3) until the disappearance of PhSCF2CF2SiMe3. F-TEDA (2.9 g, 8.2 mmol) was added to the mixture, which was stirred for 1 h at ambient temperature. The mixture was concentrated and the solid residue washed with ethyl ether (10×50 ml). The filtrate was evaporated and the product purified by bulb-to-bulb distillation. The product 2-(phenylsulfanyl)-1,1,2,2-tetrafluoroethane-sulfonyl fluoride was obtained in the form of a colorless liquid (1.86 g, 79%). prepared was stirred at ambient temperature overnight was stirred for 1 h at ambient temperature The mixture was concentrated the solid residue washed with ethyl ether (10×50 ml) The filtrate was evaporated the product purified by bulb-to-bulb distillation