Water → 4-[(4-Chlorobenzyl)sulfonyl]-1,2-difluorobenzene

HRID 1686428Notes

Reaction equation

HRID 1686428 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-:20].[K+].[K+].[OH2:25]>CN(C=O)C>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)(=[O:20])=[O:25])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 27783783,4-Difluorobenzenethiol

Product 1

HCID 689551304-[(4-Chlorobenzyl)sulfonyl]-1,2-difluorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4-difluorobenzenethiol (1.0 g), 1-(bromomethyl)-4-chlorobenzene (1.28 g) and potassium carbonate (0.94 g) in DMF (10 ml) was stirred overnight at RT then diluted with water, extracted with ether, and the organics dried (MgSO4) and evaporated under reduced pressure. The resulting oil was dissolved in DCM (10 ml) and MCPBA (2.94 g) added and stirred at RT overnight. The solution was then washed with aqueous sodium metabisulphite and aqueous sodium hydrogen carbonate, dried (MgSO4) and evaporated under reduced pressure to give a solid, triturated with isohexane to give the subtitle compound as a white solid (2.3 g).

Workup

  1. extractionextracted with ether
  2. dry with materialthe organics dried (MgSO4)
  3. customevaporated under reduced pressure
  4. dissolutionThe resulting oil was dissolved in DCM (10 ml)
  5. additionMCPBA (2.94 g) added
  6. washThe solution was then washed with aqueous sodium metabisulphite and aqueous sodium hydrogen carbonate
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure
  9. customto give a solid
  10. customtriturated with isohexane

Sources & evidence

ORD record
ord-be0ac17b18fe42e5ad79018a15ea30a6
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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