Tert-butyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate → 3-(2-Chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole
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(C)(C)C)=O)[N:15]=1>C(OCC)(=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]=1Participants
3
Procedure
To an ethyl acetate (100 mL) solution of tert-butyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate (49.7 g, 126 mmol) was added 3 mol/L of HCL (40 mL), and the mixture was refluxed under heating for 2 hours. After completion of the reaction, the reaction mixture was consecutively washed with water and a 1 mol/L sodium hydroxide aqueous solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off to give a white solid of 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole (33.0 g, yield: 89.0%). Melting point: 116˜117° C., 1H-NMR (CDCl3, TMS, ppm): δ2.24 (s, 3H), 5.69 (s, 1H), 7.36 (dd, J=1.8 Hz, JHF=9.4 Hz, 1H), 7.50-7.60 (m, 1H), 9.00-9.30 (brs, 1H).
Workup
- temperaturethe mixture was refluxed
- temperatureunder heating for 2 hours
- customAfter completion of the reaction
- washthe reaction mixture was consecutively washed with water
- dry with materiala 1 mol/L sodium hydroxide aqueous solution and dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off
Sources & evidence
- ORD record
- ord-342196a38a7e457c9688c647f4c23adb
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767827B2
Reaction notes
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