Water → HCID 58046308, compound

HRID 2359317Notes

Reaction equation

HRID 2359317 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:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]=1[C:31]([F:34])([F:33])[F:32].O>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([O:30][C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[C:25]([C:31]([F:34])([F:32])[F:33])[CH:26]=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

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 58042499tert-butyl 5-chloro-2,4-difluorobenzoate

Product 1

HCID 58046308HCID 58046308, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of tert-butyl 5-chloro-2,4-difluorobenzoate (Preparation 51, 200 mg, 0.80 mmol) in DMSO (4 mL) was added K2CO3 (333 mg, 2.41 mmol) followed by 4-chloro-3-(trifluoromethyl)phenol (190 mg, 0.97 mmol) and the reaction stirred at room temperature for 18 h. Water (10 mL) and EtOAc (15 mL) were added and the layers separated. The aqueous layer was extracted with EtOAc (15 mL). The combined organic extracts were washed with brine (15 mL), dried (MgSO4) filtered and the solvent removed under reduced pressure to give the title compound (245 mg, 72%) as a solid.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with EtOAc (15 mL)
  3. washThe combined organic extracts were washed with brine (15 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4684b150f11f4bde968e733cfca54efa
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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