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

HRID 1395956Notes

Reaction equation

HRID 1395956 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>C(#N)C>[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

5

Reactant 3

HCID 6344DichloromethaneHCID 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 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate (2.00 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, de-ionized water. The mixture was stirred vigorously for 36 hours. Stirring was stopped and the mixture separated into two clear layers; the organic layer was washed twice with 30 mL 1% aqueous ammonium hydroxide and five times with 30 mL of distilled, de-ionized water. Hydroquinone (1 mg) was added and dichloromethane was removed by rotary evaporation to yield the product as a colorless, viscous oil (2.65 g, 4.76 mmol; 80% yield). The oil was dissolved in acetonitrile (50 wt %) (3.9 g). 1H NMR (500 MHz, acetone-d6) δ 8.0 (m, 15H), 6.1 (s, 1H), 5.6 (s, 1H), 4.4 (t, 2H), 3.8 (m, 2H), 1.9 (s, 3H). 19F NMR (300 MHz, acetone-d6) δ −112.7 (s, 2F), −119.8 (s, 2F).

Workup

  1. distillationof distilled
  2. stirringStirring
  3. customthe mixture separated into two clear layers
  4. washthe organic layer was washed twice with 30 mL 1% aqueous ammonium hydroxide and five times with 30 mL
  5. distillationof distilled
  6. additionHydroquinone (1 mg) was added
  7. customdichloromethane was removed by rotary evaporation
  8. customto yield the product as a colorless, viscous oil (2.65 g, 4.76 mmol; 80% yield)

Sources & evidence

ORD record
ord-c0449b5f51f74f84a0eae95b16ea9ca1
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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