Triphenylsulfonium chloride → Triphenylsulfonium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate

HRID 908078Notes

Reaction equation

HRID 908078 reaction equation
[C:1]12([C:11]([O:13][CH2:14][C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:18])=[O:17])=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Na+].[Cl-].[C:24]1([S+:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:1]12([C:11]([O:13][CH2:14][C:15]([F:21])([F:20])[S:16]([O-:19])(=[O:17])=[O:18])=[O:12])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2.[C:37]1([S+:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chlorideHCID 57872247Sodium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate

Product 1

HCID 25229891Triphenylsulfonium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 g of dichloromethane were dissolved 10 g (0.02 mole) of sodium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate (purity 70%) and 50 g (0.02 mole) of a triphenylsulfonium chloride aqueous solution. The organic layer was separated, washed three times with 20 g of water, and concentrated. Diethyl ether was added to the residue for recrystallization, obtaining the target compound as white crystals. 10 g (yield 85%).

Workup

  1. customThe organic layer was separated
  2. washwashed three times with 20 g of water
  3. concentrationconcentrated
  4. additionDiethyl ether was added to the residue for recrystallization

Sources & evidence

ORD record
ord-944f7e24a5364a36908f1a1d1501c534
Source dataset
uspto-grants-2011_09
Patent number
US08017302B2

Reaction notes

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