Dichloromethane → (t-Butylphenyl)(diphenyl)sulfonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate

HRID 1395952Notes

Reaction equation

HRID 1395952 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]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S+:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH3:26])([CH3:25])[CH3:24].ClCCl>O>[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]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S+:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 86667399(t-Butylphenyl)(diphenyl)sulfonium bromide

Product 1

HCID 86667398(t-Butylphenyl)(diphenyl)sulfonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonateYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylammonium 1,1-difluoro-2-(methacryloyl-oxy)ethane-1-sulfonate (5.00 g, 15.1 mmol) and (t-butylphenyl)(diphenyl)sulfonium bromide (6.00 g, 15.0 mmol) were added to a 100 mL round bottom flask, along with 30 mL of dichloromethane and 30 mL of 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 once with 30 mL 0.1% aqueous hydrochloric acid and four times with 30 mL of de-ionized water. Hydroquinone (1 mg) was added and dichloromethane was removed by rotary evaporation to yield the product as a colorless, viscous oil (7.2 g, 87% yield). The oil was dissolved to 40 wt % in acetonitrile for further use. 1H NMR (500 MHz, acetone-d6) δ 7.9 (m, 14H), 6.1 (s, 1H), 5.7 (s, 1H), 4.7 (m, 2H), 1.9 (s, 3H), 1.3 (s, 9H). 19F NMR (300 MHz, acetone-d6) δ −115.7 (s, 2F).

Workup

  1. stirringStirring
  2. customthe mixture separated into two clear layers
  3. washthe organic layer was washed once with 30 mL 0.1% aqueous hydrochloric acid and four times with 30 mL of de-ionized water
  4. additionHydroquinone (1 mg) was added
  5. customdichloromethane was removed by rotary evaporation

Sources & evidence

ORD record
ord-59e89895cca3442398cc7510abdcd43f
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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