Benzoyl Peroxide → Sodium 1,1-difluoro-2-tosyloxyethanesulfonate

HRID 491248

Reaction equation

HRID 491248 reaction equation
[S:1]([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)([O:4][CH:5]=[C:6]([F:8])[F:7])(=[O:3])=[O:2].[S:16]([O-:19])([OH:18])=[O:17].[Na+:20].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O.CO>[F:8][C:6]([F:7])([S:16]([O-:19])(=[O:18])=[O:17])[CH2:5][O:4][S:1]([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(=[O:3])=[O:2].[Na+:20]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 109773662,2-Difluoroethenyl 4-methylbenzene-1-sulfonateHCID 23665763Sodium Bisulfite

Product 1

HCID 86612196Sodium 1,1-difluoro-2-tosyloxyethanesulfonateYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

9.3 g of 2,2-difluoroethenyl tosylate, which had been synthesized by a conventional technique, was dispersed in 17 g of water and 37 g of methanol, after which 4.7 g of sodium hydrogen sulfite and 0.5 g of benzoyl peroxide were added. The reaction mixture was stirred at 80° C. for 40 hours. The reaction solution was allowed to cool, after which methanol was distilled off in vacuum. Toluene was added, followed by separatory operation to separate a water layer. A saturated sodium chloride aqueous solution was added to the water layer whereupon white crystals settled out. The crystals were collected by filtration, washed with a small volume of saturated sodium chloride aqueous solution and then dried in vacuum, obtaining the target compound, sodium 1,1-difluoro-2-tosyloxyethanesulfonate. White crystals, 2.5 g (yield 16%).

Workup

  1. temperatureto cool
  2. distillationafter which methanol was distilled off in vacuum
  3. additionToluene was added
  4. customto separate a water layer
  5. additionA saturated sodium chloride aqueous solution was added to the water layer whereupon white crystals
  6. filtrationThe crystals were collected by filtration
  7. washwashed with a small volume of saturated sodium chloride aqueous solution
  8. customdried in vacuum

Sources & evidence

ORD record
ord-4691630394ac41cbaeb1d3a0205ceffb
Source dataset
uspto-grants-2009_05
Patent number
US07531290B2

Linked notes

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