(4-tert-Butylphenyl)(diphenyl)sulfanium bromide → 4-Tert-butylphenyldiphenylsulfonium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate

HRID 1670362Notes

Reaction equation

HRID 1670362 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+].[Br-].[C:24]([C:28]1[CH:33]=[CH:32][C:31]([S+:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:30][CH:29]=1)([CH3:27])([CH3:26])[CH3:25]>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:24]([C:28]1[CH:33]=[CH:32][C:31]([S+:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:30][CH:29]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 22625536(4-tert-Butylphenyl)(diphenyl)sulfanium bromideHCID 57872247Sodium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonate

Product 1

HCID 866327554-Tert-butylphenyldiphenylsulfonium 2-(1-adamantanecarbonyloxy)-1,1-difluoroethanesulfonateYield 86%

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-difluoro-ethanesulfonate (purity 70%) and 80 g (0.02 mole) of a 4-tert-butylphenyldiphenylsulfonium bromide 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. 11 g (yield 86%).

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-09f48005849646ea95c290ebc4b35c14
Source dataset
uspto-grants-2011_08
Patent number
US07993811B2

Reaction notes

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