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

HRID 1395957Notes

Reaction equation

HRID 1395957 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-sulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Potassium 1,1,2,2-tetrafluoro-4-(methacryloyloxy)butane-1-sulfonate, synthesized as described above, (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 stirred vigorously over the weekend. 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 white solid (2.41 g, 4.35 mmol). 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

Sources & evidence

ORD record
ord-b0ec2162f2bf4d2d81f9cba567fb4b91
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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