Triphenylsulfonium chloride → Triphenylsulfonium 1,1-difluoro-2-tosyloxyethanesulfonate

HRID 491249Notes

Reaction equation

HRID 491249 reaction equation
[Cl-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:21][C:22]([F:39])([S:35]([O-:38])(=[O:37])=[O:36])[CH2:23][O:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26].[Na+]>ClCCl>[F:39][C:22]([F:21])([S:35]([O-:38])(=[O:37])=[O:36])[CH2:23][O:24][S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:32])=[CH:33][CH:34]=1)(=[O:27])=[O:26].[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chlorideHCID 86612196Sodium 1,1-difluoro-2-tosyloxyethanesulfonate

Product 1

HCID 86612197Triphenylsulfonium 1,1-difluoro-2-tosyloxyethanesulfonateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 62 g of dichloromethane were added an amount (corresponding to 0.031 mole) of the triphenylsulfonium chloride aqueous solution of Synthesis Example 1 and 1.1 g (0.033 mole) of sodium 1,1-difluoro-2-tosyloxyethanesulfonate synthesized in Synthesis Example 9, followed by stirring. The organic layer was separated and washed with 20 g of water three times. The organic layer was concentrated and 10 g of diisopropyl ether was added to the residue for crystallization. The crystals were filtered and dried, obtaining the target compound. White crystals, 1.3 g (yield 74%).

Workup

  1. customsynthesized in Synthesis Example 9
  2. customThe organic layer was separated
  3. washwashed with 20 g of water three times
  4. concentrationThe organic layer was concentrated
  5. addition10 g of diisopropyl ether was added to the residue for crystallization
  6. filtrationThe crystals were filtered
  7. customdried
  8. customobtaining the target compound

Sources & evidence

ORD record
ord-497033c00cf94772b16745e935eee3ec
Source dataset
uspto-grants-2009_05
Patent number
US07531290B2

Reaction notes

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