Hydrochloric Acid → 3-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

HRID 644837Notes

Reaction equation

HRID 644837 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:12]=[C:11]([CH3:13])[NH:10][N:9]=1.[Cl:14][C:15]1[CH:16]=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:18]=[C:19]([Cl:22])[C:20]=1F.Cl>CN(C=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:18]=[C:19]([Cl:22])[C:20]=1[O:7][C:8]1[CH:12]=[C:11]([CH3:13])[NH:10][N:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-HCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 178623603-(2,6-Dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazoleYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (2.8 g, 20.0 mmol) was added to a solution of 3-hydroxy-5-methylpyrazole (1.47 g, 15.0 mmol) and 3,5-dichloro-4-fluorobenzotrifluoride (3.5 g, 15.0 mmol) in DMF (30 ml), and the mixture was stirred under heating at 60° C. for 6 hours. After completion of the reaction, the reaction mixture was poured into 2N hydrochloric acid (70 ml) and extracted with ethyl acetate (30 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10→1/7), to give a white solid of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (2.5 g, yield: 54.0%). mp: 153-155° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.27 (s, 3H), 5.68 (s, 1H), 7.64 (s, 2H), 8.75-9.70 (br s, 1H).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (30 ml×3)
  3. washAn organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customto remove a desiccant, and the solvent
  7. distillationwas distilled off from the filtrate under reduced pressure
  8. customThe resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10→1/7)

Sources & evidence

ORD record
ord-8e6b3c3fdce54262be3245abfc20e3c2
Source dataset
uspto-grants-2010_04
Patent number
US07700786B2

Reaction notes

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