Water → HCID 18347218, compound

HRID 2269568Notes

Reaction equation

HRID 2269568 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[O:11].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[C:1]1([S:7][CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 18347218HCID 18347218, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of thiophenol (5.5 g) and 2-bromo-1-(4-(methanesulfonyl)phenyl)ethanone (14.8 g) in acetone (250 mL) was added K2CO3 (13.8 g). The mixture was stirred at r.t. for 1 hr then H2O added and the solution was extracted with EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. The residue was triturated in EtOAc/Et2O, filtered and air dried, giving 13.4 g of the title compound.

Workup

  1. extractionthe solution was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated under vacuum
  6. customThe residue was triturated in EtOAc/Et2O
  7. filtrationfiltered
  8. customair dried

Sources & evidence

ORD record
ord-20db92cbbf214ba78fc43033692e86df
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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