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

HRID 1021009Notes

Reaction equation

HRID 1021009 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].[K+].[Br-].[C:21]1([S+:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl>[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:34]1([S+:27]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 11984010Triphenylsulfonium BromideHCID 86667402Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate

Product 1

HCID 86660804Triphenylsulfonium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonateYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate (2 g, 6.02 mmol) and triphenylsulfonium bromide (2.25 g, 6.57 mmol) were added to a 100-mL round bottom flask, along with 15 mL of dichloromethane and 15 mL of distilled, deionized water. The mixture was vigorously stirred for 36 hours. Stirring was stopped and the mixture separated into two clear layers; the organic layer was washed twice with 30 mL of 1% (w/w) aqueous ammonium hydroxide and five times with 30 mL of distilled, de-ionized water. The organic layer was dried over sodium sulfate and filtered. Hydroquinone (1 mg) was added and the solvent was removed by rotary evaporation and high vacuum to yield the product as a colorless, viscous oil (2.65 g, 4.76 mmol). 1H NMR (d6-acetone): 7.9 (br), 6.1 (s), 5.6 (s), 4.4 (t), 2.8 (m), 1.9 (s); 19F NMR (d6-acetone): −112.7 (s), −119.7 (s).

Workup

  1. distillationof distilled
  2. stirringStirring
  3. customthe mixture separated into two clear layers
  4. washthe organic layer was washed twice with 30 mL of 1% (w/w) aqueous ammonium hydroxide and five times with 30 mL
  5. distillationof distilled
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. additionHydroquinone (1 mg) was added
  9. customthe solvent was removed by rotary evaporation and high vacuum

Sources & evidence

ORD record
ord-7af3047e5873404781325298de334497
Source dataset
uspto-grants-2014_05
Patent number
US08716518B2

Reaction notes

Loading…