Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonate → (t-Butylphenyl)(phenyl)iodonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate

HRID 1395953Notes

Reaction equation

HRID 1395953 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.C([O-])(=O)C.[C:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[I+:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:29])([CH3:28])[CH3:27]>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:26]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[I+:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 86660800Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethanesulfonateHCID 88548156(t-Butylphenyl)(phenyl)iodonium acetate

Product 1

HCID 88548194(t-Butylphenyl)(phenyl)iodonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylammonium 1,1-difluoro-2-(methacryloyloxy)ethane-1-sulfonate (5.00 g, 15.1 mmol) and (t-butylphenyl)(phenyl)iodonium acetate (5.98 g, 15.1 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, then stopped and the mixture separated into two clear layers; the organic layer was washed once with 30 mL 1% (w/w) aqueous hydrochloric acid and four times with 30 mL of de-ionized water. Hydroquinone (1 mg) was added and dichloromethane removed by rotary evaporation to yield the product as a colorless, viscous oil (7.6 g, 89% yield). The oil was dissolved to 50 wt % in acetonitrile. 1H NMR (500 MHz, acetone-d6) δ 8.4 (d, 2H), 8.3 (d, 2H), 7.7 (t, 1H), 7.6 (m, 4H), 6.2 (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 −115.4 (s, 2F).

Workup

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

Sources & evidence

ORD record
ord-9de1c62ec4194602bebdd3c1cd85b3e5
Source dataset
uspto-grants-2014_12
Patent number
US08900792B2

Reaction notes

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