Triphenylsulfonium Bromide → Triphenylsulfonium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate

HRID 571158Notes

Reaction equation

HRID 571158 reaction equation
[F:1][C:2]([F:18])([S:14]([O-:17])(=[O:16])=[O:15])[C:3]([F:13])([F:12])[CH2:4][CH2:5][O:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9].C([NH+](CC)CC)C.[Br-].[C:27]1([S+:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)(Cl)Cl>[F:18][C:2]([F:1])([S:14]([O-:17])(=[O:16])=[O:15])[C:3]([F:13])([F:12])[CH2:4][CH2:5][O:6][C:7](=[O:11])[C:8]([CH3:10])=[CH2:9].[C:40]1([S+:33]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 2

HCID 11984010Triphenylsulfonium BromideHCID 86660803Triethylammonium 1,1,2,2-tetrafluoro-4-(2-methyl-acryloyloxy)-butane-1-sulfonate

Product 1

HCID 86660804Triphenylsulfonium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonateYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 100 mL reactor was charged with the aqueous solution of triethylammonium 1,1,2,2-tetrafluoro-4-(2-methyl-acryloyloxy)-butane-1-sulfonate obtained by the 3rd step, and a solution of 20.2 g (0.056 mole) of triphenylsulfonium bromide and 100 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 100 g of water four times. Subsequently, it was rinsed with 100 g of diisopropyl ether three times thereby precipitating a solid. Upon performing filteration, the solid was dried, thereby obtaining 32.5 g of a target triphenylsulfonium 1,1,2,2-tetrafluoro-4-(2-methyl-acryloyloxy)-butane-1-sulfonate. It exhibited a purity of 93% at this time (most of a balance of 7% was the solvent, i.e., diisopropyl ether), and a yield of 97% 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 100 g of water four times
  4. washSubsequently, it was rinsed with 100 g of diisopropyl ether three times
  5. customthereby precipitating a solid
  6. customthe solid was dried

Sources & evidence

ORD record
ord-e9fc019a91eb4ee8b8479543fdbfdeb8
Source dataset
uspto-grants-2015_05
Patent number
US09024058B2

Reaction notes

Loading…