Sodium Hydroxide → 3-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole

HRID 499994Notes

Reaction equation

HRID 499994 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([F:12])[C:3]=1[O:13][C:14]1[CH:18]=[C:17]([CH3:19])[N:16](C(OC)=O)[N:15]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[C:4]([F:12])[C:3]=1[O:13][C:14]1[CH:18]=[C:17]([CH3:19])[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57548572Methyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate

Product 1

HCID 178624283-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazoleYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (10 mL) solution of methyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate (0.53 g, 1.5 mmol) was added 5% sodium hydroxide (8 mL), and the mixture was refluxed under heating for 2 hours. After completion of the reaction, the solvent was distilled off the reaction mixture, and then water was added, followed by extraction with ethyl acetate. The organic layers combined were washed with water, and dried over anhydrous magnesium sulfate and the solvent was distilled off. The resultant residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give a white solid of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.39 g, yield: 88.2%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off the reaction mixture
  5. additionwater was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layers combined were washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe resultant residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-168435d52cd24c1d876f2a0a3608e765
Source dataset
uspto-grants-2010_08
Patent number
US07767827B2

Reaction notes

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