Potassium Carbonate → HCID 18467013, compound

HRID 2229263Notes

Reaction equation

HRID 2229263 reaction equation
F[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:18][SH:19]>CN(C=O)C.O>[F:10][C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:18]([C:17]([O:21][CH2:22][CH3:23])=[O:20])[S:19][C:2]=2[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 737702,4-Difluorobenzaldehyde

Product 1

HCID 18467013HCID 18467013, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,4-difluorobenzaldehyde (50.17 g) and potassium carbonate (63.4 g) in DMF (500 ml) was added ethyl thioglycolate (38.7 ml) dropwise at 0° C. The mixture was stirred at room temperature for 18 hours, diluted with water, and extracted with ethyl acetate. The extract was washed with 10% aqueous citric acid, water, and brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica gel using hexane-ethyl acetate (20:1) as an eluent to give the titled compound as colorless crystals (16.61 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
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-4c7f029693b846519c77a2eb40b318f5
Source dataset
uspto-grants-2002_07
Patent number
US06420375B1

Reaction notes

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