Water → HCID 87355576, compound

HRID 1182640Notes

Reaction equation

HRID 1182640 reaction equation
[C:1]([O:6][CH2:7][C:8]([O:10][CH2:11][C:12]([F:18])([F:17])[S:13]([O-:16])(=[O:15])=[O:14])=[O:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[Na+].O.[Br-].[C:22]1([S+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[C:1]([O:6][CH2:7][C:8]([O:10][CH2:11][C:12]([F:18])([F:17])[S:13]([O-:16])(=[O:14])=[O:15])=[O:9])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:35]1([S+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11984010Triphenylsulfonium BromideHCID 58352295HCID 58352295, compound

Product 1

HCID 87355576HCID 87355576, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a 200-mL reaction vessel, 5.77 g (purity: 44%, 8.56 mmol) of sodium 2-[(methacryloyloxy)acetoxy]-1,1-difluoroethanesulfonate obtained in Preparation Example 2-1, 15 mL of water and 15 mL of chloroform were added. Then, 2.9 g (8.6 mmol) of triphenylsulfonium bromide was dropped into the reaction vessel at room temperature. The resulting solution was stirred for 2 hours at room temperature and subjected to separation. The thus-obtained organic phase was washed with 15 mL of water and subjected to solvent evaporation, thereby obtaining 3.58 g of target triphenylsulfonium 2-[(methacryloyloxy)acetoxy]-1,1-difluoroethanesulfonate as a crude product. The purity of the crude target product was 57%; and the yield of the crude target product was 76%. The obtained crude triphenylsulfonium 2-[(methacryloyloxy)acetoxy]-1,1-difluoroethanesulfonate was admixed with 6 g of chloroform, 3 g of ethyl acetate and 1.5 g of diisopropyl ether and totally dissolved in the solvent by heating. The resulting solution was cooled in air, thereby precipitating a solid out of the solution. The precipitated solid was filtered out and dried. With this, 2.32 g of the target 2-[(methacryloyloxy)acetoxy]-1,1-difluoroethanesulfonate was obtained with a purity of 98%.

Workup

  1. additionwere added
  2. customsubjected to separation
  3. washThe thus-obtained organic phase was washed with 15 mL of water
  4. customsubjected to solvent evaporation

Sources & evidence

ORD record
ord-f2b54bd1b52348808efad99f14e9ecb4
Source dataset
uspto-grants-2014_03
Patent number
US08663897B2

Reaction notes

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