Triphenylsulfonium Bromide → Triphenylsulfonium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethane-1-sulfonate

HRID 571155Notes

Reaction equation

HRID 571155 reaction equation
[F:1][C:2]([F:14])([S:10]([O-:13])(=[O:12])=[O:11])[CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].C([NH+](CC)CC)C.[Br-].[C:23]1([S+:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[F:14][C:2]([F:1])([S:10]([O-:13])(=[O:12])=[O:11])[CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].[C:36]1([S+:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 11984010Triphenylsulfonium BromideHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate

Product 1

HCID 86648110Triphenylsulfonium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethane-1-sulfonateYield 87%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 50 mL reactor was charged with the triethylammonium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethane-1-sulfonate aqueous solution obtained by the 3rd step, and a solution of 3.18 g (8.9 millimoles) of triphenylsulfonium bromide and 20 g of chloroform, followed by 3 hours of stirring at room temperature. Subsequently, an organic layer was separated, and the thus obtained organic layer was rinsed with 20 g of water four times. Subsequently, it was rinsed with 20 g of diisopropyl ether three times and then a volatile component was distilled off, thereby obtaining 3.92 g of a target triphenylsulfonium 1,1-difluoro-2-(2-methyl-acryloyloxy)-ethane-1-sulfonate. It exhibited a purity of 97% at this time, and a yield of 87% taken over from the 3rd step.

Workup

  1. customobtained by the 3rd step
  2. customSubsequently, an organic layer was separated
  3. washthe thus obtained organic layer was rinsed with 20 g of water four times
  4. washSubsequently, it was rinsed with 20 g of diisopropyl ether three times
  5. distillationa volatile component was distilled off

Sources & evidence

ORD record
ord-7a6d1b98f67a4b15876d1ce5bb9dfedd
Source dataset
uspto-grants-2015_05
Patent number
US09024058B2

Reaction notes

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