Water → 2-Chloro-1-fluoro-4-[(4-fluorobenzyl)sulfonyl]benzene

HRID 1686413Notes

Reaction equation

HRID 1686413 reaction equation
[Cl: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]([F:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-:20].[K+].[K+].[OH2:25]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)(=[O:20])=[O:25])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 27341973-Chloro-4-fluorobenzene-1-thiol

Product 1

HCID 689534292-Chloro-1-fluoro-4-[(4-fluorobenzyl)sulfonyl]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-4-fluorobenzenethiol (1.0 g), 1-(bromomethyl)-4-fluorobenzene (1.15 g) and potassium carbonate (0.85 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 (1.2 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 an oil which was purified by flash column chromatography (eluting 3:2 i-hexane/ether) to give the subtitle compound as a white solid (1.3 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 (1.2 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 an oil which
  10. customwas purified by flash column chromatography (eluting 3:2 i-hexane/ether)

Sources & evidence

ORD record
ord-357906e1219e453d9495bb7f3e45b987
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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