Water → 4-iodo-1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole

HRID 2243251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2243251
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[I:13][C:14]1[C:15]([C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])=[N:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[I:13][C:14]1[C:15]([C:19]([F:25])([F:24])[C:20]([F:21])([F:22])[F:23])=[N:16][N:17]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 178506332HCID 178506332, Verbindung

Produkt 1

HCID 866171374-iodo-1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazoleAusbeute 21,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Methyl-4-nitrobenzyl chloride (8.57 g), 4-iodo-3-pentafluoroethyl-1H-pyrazole (16.00 g) and potassium carbonate (7.66 g) were stirred in DMF (70 ml) at 70° C. for 1 hour. After cooling, the reaction solution was poured into water and extracted with ethyl acetate. The organic phase was washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with sodium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 4-iodo-1-(3-methyl-4-nitrobenzyl)-3-pentafluoroethyl-1H-pyrazole (4.60 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialAfter drying the organic layer with sodium sulfate
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-287f8efea3f040648c86270815814dc3
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674807B2

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