Water → HCID 58046300, compound

HRID 2359334Notes

Reaction equation

HRID 2359334 reaction equation
[Cl:1][C:2]1[C:3](F)=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:8].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28]([F:31])([F:30])[F:29].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[C:3]([O:27][C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:23]=2)=[CH:4][C:5]([F:18])=[C:6]([CH:17]=1)[C:7]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:8]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 58042518HCID 58042518, compound

Product 1

HCID 58046300HCID 58046300, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 10, 39.0 g, 137.97 mmol) and 4-chloro-3-(trifluoromethyl)phenol (27.12 g, 137.97 mmol) in DMSO (197 mL) was added potassium carbonate (47.67 g, 344.92 mmol) portion wise maintaining the internal at 15-25° C. with a cold water jacket. The reaction mixture was stirred at room temperature for 2 hours, cold water charged and the resulting slurry stirred for 20 minutes. The mixture was filtered, washed with water and dried to give the title compound as a pale yellow solid (56.4 g, 90%).

Workup

  1. stirringthe resulting slurry stirred for 20 minutes
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-85e0be6ed4d443f697509681ad1a06d1
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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