Reacción #492194

ord-7d525ea3ae0e4186b6f58d6de61ff2e1

Ecuación de reacción

[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
O=S(=O)(O)C(F)(F)CO.[Na]
sodium 2-hydroxy-1,1-difluoroethanesulfonic acid
O=S(=O)(O)C(F)(F)CO.[Na]
sodium 2-hydroxy-1,1-difluoroethanesulfonic acid
O
water
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
[Cl-].c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium chloride
O=S(=O)([O-])C(F)(F)CO.c1ccc([S+](c2ccccc2)c2ccccc2)cc1
triphenylsulfonium 2-hydroxy-1,1-difluoroethanesulfonate
Rendimiento 97.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.WAITthe reaction time was 1.5 hours
  2. 2
    Otroby which the raw material was detected being consumed
  3. 3
    OtroThereafter, the reaction solution was separated
  4. 4
    ExtracciónThe obtained water layer was extracted with 100 mL of chloroform three times
  5. 5
    workup.DISTILLATIONwhile distilling a solvent out of the obtained organic layer

Procedimiento

A 2 L reactor was charged with 183.7 g (38% purity, 0.38 mole) of sodium 2-hydroxy-1,1-difluoroethanesulfonic acid, 300 mL of water, 450 mL of chloroform and an aqueous solution of triphenylsulfonium chloride [142.8 g (0.49 mole/1.25 equivalents) of triphenylsulfonium chloride and 150 mL of water], followed by stirring at room temperature for 1 hour. A reaction solution was analyzed by using nuclear magnetic resonance (NMR), by which there was found almost half the raw material sodium 2-hydroxy-1,1-difluoroethanesulfonic acid remaining. Accordingly, the reactor was further charged with the aqueous solution of triphenylsulfonium chloride [142.8 g (0.49 mole/1.25 equivalents) of triphenylsulfonium chloride and 150 mL of water], followed by stirring at room temperature for 0.5 hour (triphenylsulfonium chloride was used in an amount of 285.7 g (0.96 mole/2.5 equivalents) in total and the reaction time was 1.5 hours in total). The reaction solution was analyzed by using nuclear magnetic resonance (NMR), by which the raw material was detected being consumed. Thereafter, the reaction solution was separated. The obtained water layer was extracted with 100 mL of chloroform three times while distilling a solvent out of the obtained organic layer, thereby obtaining 328.2 g of the target triphenylsulfonium 2-hydroxy-1,1-difluoroethanesulfonate. In this case, the purity was 48% and the yield was 97%.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08748672B2uspto-grants-2014_06