Water → HCID 18467045, compound

HRID 2229262Notes

Reaction equation

HRID 2229262 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[SH:9].Cl[CH2:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:11][C:12](=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 27370732,4-Difluorobenzene-1-thiol

Product 1

HCID 18467045HCID 18467045, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,4-difluorothiophenol (4.95 g) and chloroacetone (2.8 ml) in DMF (30 ml) was added potassium carbonate (9.67 g) at 0° C. The mixture was stirred for 3 hours, poured into water, and extracted with ethyl acetate. The extract was washed with 10% aqueous citric acid, water, and brine, dried over MgSO4, and concentrated to give 1-(2,4-difluorophenylthio)propan-2-one (6.80 g). This compound was dissolved in toluene and heated at reflux for 30 hours with polyphosphoric acid (24 g). The solvent was evaporated, and the mixture was heated at 150° C. for 1 hour, carefully neutralized with aqueous potassium carbonate with ice-cooling, and extracted with ethyl acetate. The extract was washed with water and brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica gel using hexane as an eluent to give the titled compound as colorless crystals (2.00 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 10% aqueous citric acid, water, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad8b3199403e4e28b3d094930e477473
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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