Sodium Iodide → Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate

HRID 556246

Reaction equation

HRID 556246 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([C:16]([F:19])([F:18])[F:17])[C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:12])=[O:11])=[O:6].[C:20]1([S+:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:39]([O-:44])(=[O:43])[C:40]([CH3:42])=[CH2:41].[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:14][C:9]([F:15])([S:10]([O-:13])(=[O:12])=[O:11])[CH:8]([O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][O:44][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41])[C:16]([F:19])([F:18])[F:17].[C:33]1([S+:26]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 83982,2'-Methylenebis(4-methyl-6-tert-butylphenol)HCID 3255932Sodium methacrylateHCID 86639509Triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

Product 1

HCID 86639511Triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To 20 g of dimethylformamide were added 5.4 g (9.0 mmol) of triphenylsulfonium 2-(4-chlorobutyryloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate synthesized in Synthesis Example 1-20, 1.2 g (11 mmol) of sodium methacrylate, 0.20 g (1.4 mmol) of sodium iodide, and 1 mg of 2,2′-methylenebis(6-t-butyl-p-cresol). The mixture was heated and stirred at 90° C. for 12 hours. The reaction solution was allowed to resume room temperature, after which 50 g of water and 80 g 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 30 g of methyl isobutyl ketone and washed with water whereupon methyl isobutyl ketone was distilled off under vacuum. The residue was purified by silica gel chromatography. The target compound, triphenylsulfonium 1,1,3,3,3-pentafluoro-2-(4-methacryloyloxy-butyryloxy)-propane-1-sulfonate was obtained as brown oil (4.2 g, yield 72%). 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 water whereupon methyl isobutyl ketone
  7. distillationwas distilled off under vacuum
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7d4dbbd4c503453a849660fd9226dbcb
Source dataset
uspto-grants-2011_11
Patent number
US08057985B2

Linked notes

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