Sodium Iodide → Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(2-methacryloyloxy-acetoxy)-propane-1-sulfonate

HRID 556245

Reaction equation

HRID 556245 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]([C:14]([F:17])([F:16])[F:15])[C:7]([F:13])([F:12])[S:8]([O-:11])(=[O:10])=[O:9])=[O:4].[C:18]1([S+:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:37]([O-:42])(=[O:41])[C:38]([CH3:40])=[CH2:39].[Na+].[I-].[Na+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)C1C(O)=C(C(C)(C)C)C=C(C)C=1>ClCCl.O.CN(C)C=O>[F:12][C:7]([F:13])([S:8]([O-:11])(=[O:10])=[O:9])[CH:6]([O:5][C:3](=[O:4])[CH2:2][O:42][C:37](=[O:41])[C:38]([CH3:40])=[CH2:39])[C:14]([F:17])([F:16])[F:15].[C:31]1([S+:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 3255932Sodium methacrylateHCID 86639508Triphenylsulfonium 2-(2-chloroacetoxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

Product 1

HCID 86639510Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(2-methacryloyloxy-acetoxy)-propane-1-sulfonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To 250 g of dimethylformamide were added 50.0 g (0.09 mole) of triphenylsulfonium 2-(2-chloroacetoxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 1-19, 11.4 g (0.11 mole) of sodium methacrylate, 2.6 g (0.02 mole) of sodium iodide, and 50 mg of 2,2′-methylenebis(6-t-butyl-p-cresol). The mixture was heated and stirred at 80° C. for 13 hours. The reaction solution was allowed to resume room temperature, after which 500 g of water and 1 kg of dichloromethane were added. The organic layer was separated and washed with water whereupon dichloromethane was distilled off under vacuum. The residue was combined with 300 g of methyl isobutyl ketone, washed with dilute aqueous ammonia and then with water, whereupon methyl isobutyl ketone was distilled off under vacuum. The residue was purified by silica gel chromatography. Diisopropyl ether was added to the residue, followed by decantation. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(2-methacryloyloxy-acetoxy)-propane-1-sulfonate was obtained as brown oil (39.3 g, yield 66%). The compound has the following structure.

Workup

  1. temperatureThe mixture was heated
  2. customto resume room temperature
  3. customThe organic layer was separated
  4. washwashed with water whereupon dichloromethane
  5. distillationwas distilled off under vacuum
  6. washwashed with dilute aqueous ammonia
  7. distillationwith water, whereupon methyl isobutyl ketone was distilled off under vacuum
  8. customThe residue was purified by silica gel chromatography
  9. additionDiisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-276d9c623aef487b8e1e8c80edf5d505
Source dataset
uspto-grants-2011_11
Patent number
US08057985B2

Linked notes

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