Potassium Carbonate → HCID 58046345, compound

HRID 2359330Notes

Reaction equation

HRID 2359330 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[CH:25]=[C:26]([SH:31])[CH:27]=[CH:28][C:29]=1[Cl:30]>CS(C)=O>[Cl:1][C:2]1[C:3]([S:31][C:26]2[CH:27]=[CH:28][C:29]([Cl:30])=[C:24]([Cl:23])[CH:25]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 799643,4-DichlorobenzenethiolHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 58046345HCID 58046345, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 160, 416 mg, 1.68 mmol) was added to a mixture of potassium carbonate (694 mg, 5.02 mmol), 3,4-dichlorothiophenol (300 mg, 1.77 mmol) in DMSO (16.7 mL) and the reaction stirred at room temperature for 18 hours. The reaction was quenched by addition of 0.5 N aqueous NaOH (20 mL) and EtOAc (30 mL) and the mixture partitioned. The aqueous was further extracted with EtOAc (3×10 mL), the organics combined, washed with brine (10 mL), dried (MgSO4), filtered and evaporated to give a yellow solid. Silica gel column chromatography eluting with 9:1 DCM:heptanes resulted in isolation of the title compound as a white solid (571 mg, 83%).

Workup

  1. customThe reaction was quenched by addition of 0.5 N aqueous NaOH (20 mL) and EtOAc (30 mL)
  2. customthe mixture partitioned
  3. extractionThe aqueous was further extracted with EtOAc (3×10 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give a yellow solid
  9. washSilica gel column chromatography eluting with 9:1 DCM

Sources & evidence

ORD record
ord-e8b71d00d4ae43ee9ab70b095f8d5c36
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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