Water → Sodium 2-pivaloyloxy-1,1-difluoroethanesulfonate

HRID 1515386Notes

Reaction equation

HRID 1515386 reaction equation
[F:1][C:2]([F:14])([S:11]([O-:13])=[O:12])[CH2:3][O:4][C:5](=[O:10])[C:6]([CH3:9])([CH3:8])[CH3:7].[Na+:15].[OH2:16]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[F:14][C:2]([F:1])([S:11]([O-:16])(=[O:13])=[O:12])[CH2:3][O:4][C:5](=[O:10])[C:6]([CH3:8])([CH3:9])[CH3:7].[Na+:15]

Participants

4

Reactant 2

HCID 962WaterHCID 58112902Sodium 1,1-difluoro-2-(pivaloyloxy)ethane-1-sulfinate

Product 1

HCID 57817346Sodium 2-pivaloyloxy-1,1-difluoroethanesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 26052Sodium tungstateCatalyst

Procedure

A glass flask equipped with a thermometer, a condenser and a dropping funnel was charged with 290 g (0.74 mole) of 65% purity sodium 1,1-difluoro-2-(pivaloyloxy)ethane-1-sulfinate, a catalytic amount of sodium tungstate (IV) dihydrate, 600 ml of water, followed by stirring. Then, 170 g (1.5 moles) of 30% oxygenate was added dropwise in an iced bath. After the termination of the dropping, stirring was conducted for 1 hour at room temperature. Then, the termination of the reaction was confirmed by 19F NMR. The reaction solution was concentrated and then rinsed with 500 ml of diisopropyl ether. Subsequently, filtration was conducted and a solid obtained therewith was dried, thereby obtaining 278 g of sodium 1,1-difluoro-2-(pivaloyloxy)ethanesulfonate in the form of a white solid (91% yield, 65% purity).

Workup

  1. customA glass flask equipped with a thermometer, a condenser and a dropping funnel
  2. customThen, 170 g (1.5 moles) of 30% oxygenate
  3. additionwas added dropwise in an iced bath
  4. stirringAfter the termination of the dropping, stirring
  5. concentrationThe reaction solution was concentrated
  6. washrinsed with 500 ml of diisopropyl ether
  7. filtrationSubsequently, filtration
  8. customa solid obtained
  9. customtherewith was dried

Sources & evidence

ORD record
ord-3ec29abf628443e6a279806af1fb70be
Source dataset
uspto-grants-2012_07
Patent number
US08222448B2

Reaction notes

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