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

HRID 424329

Reaction equation

HRID 424329 reaction equation
O.[C:2]([O:8][CH2:9][C:10]([F:16])([F:15])[S:11]([O-:14])(=[O:13])=[O:12])(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[Na+].[I-].[C:19]1([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[C:2]([O:8][CH2:9][C:10]([F:16])([F:15])[S:11]([O-:14])(=[O:12])=[O:13])(=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[C:32]1([S+:25]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21881071Triphenylsulfonium iodideHCID 57817346Sodium 2-pivaloyloxy-1,1-difluoroethanesulfonate

Product 1

HCID 86632753Triphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 700 g of dichloromethane and 400 g of water were dissolved 159 g (0.37 mole) of sodium 2-(pivaloyloxy)-1,1-difluoroethanesulfonate (purity 63%) and 132 g (0.34 mole) of triphenylsulfonium iodide. The organic layer was separated and washed three times with 200 g of water. The organic layer was concentrated and diethyl ether was added to the residue for recrystallization. The target compound was obtained as white crystals, 164 g (yield 95%).

Workup

  1. customThe organic layer was separated
  2. washwashed three times with 200 g of water
  3. concentrationThe organic layer was concentrated
  4. additiondiethyl ether was added to the residue for recrystallization
  5. customThe target compound was obtained as white crystals, 164 g (yield 95%)

Sources & evidence

ORD record
ord-e7a0a4c52eab4ff0a095970d86c85eb2
Source dataset
uspto-grants-2012_01
Patent number
US08105748B2

Linked notes

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