Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate → Phenyl dibenzothiophenium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate

HRID 1395954Notes

Reaction equation

HRID 1395954 reaction equation
[F:1][C:2]([F:14])([S:10]([O-:13])(=[O:12])=[O:11])[CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].C([NH+](CC)CC)C.[Br-].[C:23]1([C:29]2[C:37]3[C:36]4[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=4[SH+:34][C:33]=3[CH:32]=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[F:14][C:2]([F:1])([S:10]([O-:13])(=[O:12])=[O:11])[CH2:3][O:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].[C:23]1([C:29]2[C:37]3[C:36]4[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=4[SH+:34][C:33]=3[CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 86667401Phenyl dibenzothiophenium bromide

Product 1

HCID 86667400Phenyl dibenzothiophenium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate (4.00 g, 12.1 mmol) and phenyl dibenzothiophenium bromide (4.50 g, 31.2 mmol) were added to a 100 mL round bottom flask, along with 30 mL of dichloromethane and 30 mL of distilled, de-ionized water. The mixture was stirred vigorously overnight. Stirring was stopped and the mixture separated into two clear layers; the organic layer was washed twice with 30 mL 1% aqueous hydrochloric acid 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 solid (3.9 g, 80% yield). 1H NMR (500 MHz, CDCl3) δ 8.2 (m, 4H), 7.8 (t, 2H), 7.7 (d, 2H), 7.6 (m, 3H), 7.5 (t, 2H), 6.2 (s, 1H), 5.6 (s, 1H), 4.9 (m, 2H), 1.9 (s, 3H). 19F NMR (300 MHz, acetone-d6) δ −115.8 (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 hydrochloric acid 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-30fec4c9572f48e199d75bb593f51a09
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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