Water → HCID 58046321, compound

HRID 2359332Notes

Reaction equation

HRID 2359332 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].[Cl:14][C:15]1[C:16](F)=[CH:17][C:18]([F:28])=[C:19]([CH:27]=1)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:14][C:15]1[C:16]([O:13][C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:12])[F:10])=[C:2]([Cl:1])[CH:3]=2)=[CH:17][C:18]([F:28])=[C:19]([CH:27]=1)[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 404271083-Chloro-4-(trifluoromethoxy)phenolHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 58046321HCID 58046321, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-chloro-4-(trifluoromethoxy)phenol (22.6 g, 0.106 mol) and tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 51, 26.4 g, 0.106 mol) were dissolved in dimethlysulfoxide (105 mL). Then potassium carbonate (29.4 g, 0.213 mol) was added portionwise to the mixture, which was stirred at room temperature for 18 hours. The reaction mixture was dropped into iced water (500 mL) and stirred vigorously for 4 hours. The resulting solid was collected by filtration then taken up in isopropanol (75 mL) and water (15 mL). The reaction was heated to 55° C., then cooled down to room temperature. The resulting solid was collected by filtration to yield the title compound as an off-white white solid (35.3 g, 75%).

Workup

  1. stirringstirred vigorously for 4 hours
  2. filtrationThe resulting solid was collected by filtration
  3. temperatureThe reaction was heated to 55° C.
  4. temperaturecooled down to room temperature
  5. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-dadcef30da80419ba55cab29f243f700
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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