Hydrochloric Acid → Ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate

HRID 499992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499992
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:21]=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:23]=[C:24]([F:27])[C:25]=1F.Cl>CS(C)=O>[Cl:19][C:20]1[CH:21]=[C:22]([C:28]([F:29])([F:30])[F:31])[CH:23]=[C:24]([F:27])[C:25]=1[O:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:3]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2736496Benzene, 1-chloro-2,3-difluoro-5-(trifluoromethyl)-HCID 178473420Ethyl 5-methyl-3-oxo-2,3-dihydro-1H-pyrazole-1-carboxylate

Produkt 1

HCID 57548573Ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylateAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a DMSO (15 mL) solution of ethyl 3-hydroxy-5-methylpyrazole-1-carboxylate (1.36 g, 8.0 mmol) and potassium carbonate (1.1 g, 8.0 mmol) was added 3-chloro-4,5-difluorobenzotrifluoride (1.77 g, 8.0 mmol) and the mixture was stirred under heating at 40° C. for 8 hours. After completion of the reaction, the reaction mixture was poured into 2 mol/L hydrochloric acid (30 mL) and extracted with ethyl acetate. The organic layers combined were washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The thus-obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7˜1:5) to give a white solid of ethyl 3-(2-chloro-6-fluoro-4-trifluoromethylphenyloxy)-5-methylpyrazole-1-carboxylate (2.14 g, yield: 72.9%). Melting point: 127˜129° C., 1H-NMR (CDCl3, TMS, ppm): δ1.40 (t, J=7.1 Hz, 3H), 2.53 (d, J=0.8 Hz, 3H), 4.41 (q, J=7.1 Hz, 2H), 5.81 (d, J=0.8 Hz, 1H), 7.38 (dd, J=2.1 Hz, JHF=9.5 Hz, 1H), 7.50˜7.60 (m, 1H).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layers combined were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe thus-obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:7˜1:5)

Quellen und Nachweise

ORD-Eintrag
ord-3c0fe6d0abc24a68b3166de2320de22f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767827B2

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