2-(Bromomethyl)-1,4-difluorobenzene → 2-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

HRID 748666Notes

Reaction equation

HRID 748666 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[F:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[Na+]>C(O)CCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:2][C:3]2[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=2[F:10])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 99010282-(((4-Chlorophenyl)sulfonyl)methyl)-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Process 3: After addition of 2-bromomethyl-1,4-difluorobenzene (12.3 ml, 95.5 mmol) to a suspension of sodium 4-chlorobenzenesulfinate (19.0 g, 95.5 mmol) in butanol (200 ml), the mixture was heated under reflux for 5 hours. The solid thus precipitated was collected by filtration and dissolved in methylene chloride. The resulting solution was washed with brine, dried over MgSO4, and concentrated. The solid thus obtained was recrystallized from hexane, whereby the title compound (12.3 g, 43%) was obtained as colorless needle crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customThe solid thus precipitated
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in methylene chloride
  6. washThe resulting solution was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe solid thus obtained
  10. customwas recrystallized from hexane, whereby the title compound (12.3 g, 43%)
  11. customwas obtained as colorless needle crystals

Sources & evidence

ORD record
ord-01e3c2bf95094d5592d8098032c61a10
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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