Phenyl dibenzothiophenium bromide → Phenyl dibenzothiophenium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate

HRID 1401750Notes

Reaction equation

HRID 1401750 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([C:27]2[C:35]3[C:34]4[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=4[SH+:32][C:31]=3[CH:30]=[CH:29][CH:28]=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:21]1([C:27]2[C:35]3[C:34]4[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=4[SH+:32][C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 86667401Phenyl dibenzothiophenium bromideHCID 86667402Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate

Product 1

HCID 86667403Phenyl dibenzothiophenium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonateYield 75.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate (1.91 g, 5.75 mmol) and phenyl dibenzothiophenium bromide (2.14 g, 6.27 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 vigorously stirred over the weekend. Stirring was stopped and the mixture separated into two clear layers; the organic layer was washed twice with 30 mL of 1% aqueous ammonium hydroxide and five times with 30 mL of distilled, deionized water. Dichloromethane was removed by rotary evaporation and high vacuum to yield the product as a white powder (2.41 g, 4.35 mmol). 1H NMR (d6-acetone): 8.6 (d), 8.4 (d), 8.0 (t), 7.8 (br), 7.6 (t), 6.1 (s), 5.6 (s), 4.4 (t), 2.8 (m), 1.9 (s); 19F NMR (d6-acetone): −112.7 (s), −119.8 (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% aqueous ammonium hydroxide and five times with 30 mL
  5. distillationof distilled
  6. customDichloromethane was removed by rotary evaporation and high vacuum

Sources & evidence

ORD record
ord-7a364c87c2964e57a3ec37589afccaf4
Source dataset
uspto-grants-2014_12
Patent number
US08907122B2

Reaction notes

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