Potassium Carbonate → HCID 58046342, compound

HRID 2359291Notes

Reaction equation

HRID 2359291 reaction equation
[F:1][C:2]1[CH:9]=[C:8](F)[C:7]([CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[C:20]([F:23])([F:22])[F:21].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:8]2[C:7]([CH3:11])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([F:1])[CH:9]=2)=[CH:15][C:14]=1[C:20]([F:21])([F:22])[F:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 805204-Chloro-3-(trifluoromethyl)phenolHCID 154517142,4-Difluoro-5-methylbenzaldehyde

Product 1

HCID 58046342HCID 58046342, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-difluoro-5-methylbenzaldehyde (100 mg, 0.64 mmol) and 4-chloro-3-trifluoromethylphenol (126 mg, 0.64 mmol) in DMSO was added potassium carbonate. The reaction was stirred at room temperature for 36 hours. The reaction was diluted with ethyl acetate (30 mL) and washed with water (2×50 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified using reverse phase column chromatography eluting with acetonitrile:water (plus 0.1% aqueous formic acid) 5:95 to 100:0 to furnish the title compound as a white solid 104 mg, 49%.

Workup

  1. washwashed with water (2×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified
  5. washeluting with acetonitrile

Sources & evidence

ORD record
ord-2dcaa151cdbe4e21903a3299107b6aa5
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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