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

HRID 909971Notes

Reaction equation

HRID 909971 reaction equation
[C:1]([O:7][CH2:8][C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:12])=[O:11])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Na+].[Br-].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>ClCCl>[C:1]([O:7][CH2:8][C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:11])=[O:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 22625536(4-tert-Butylphenyl)(diphenyl)sulfanium bromideHCID 57817346Sodium 2-pivaloyloxy-1,1-difluoroethanesulfonate

Product 1

HCID 866327544-Tert-butylphenyldiphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 150 g of dichloromethane were dissolved 20 g (0.052 mole) of sodium 2-(pivaloyloxy)-1,1-difluoroethanesulfonate (purity 70%) and 217 g (0.052 mole) of a 4-tert-butylphenyl-diphenylsulfonium bromide aqueous solution. The organic layer was separated, washed three times with 50 g of water, and concentrated. Diethyl ether was added to the residue for recrystallization, obtaining the target compound as white crystals. 26 g (yield 79%).

Workup

  1. customThe organic layer was separated
  2. washwashed three times with 50 g of water
  3. concentrationconcentrated
  4. additionDiethyl ether was added to the residue for recrystallization

Sources & evidence

ORD record
ord-1a94ca3637b74aba8a58191c65b011e2
Source dataset
uspto-grants-2011_09
Patent number
US08021822B2

Reaction notes

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