3-Bromophenylhydrazine hydrochloride → ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate

HRID 733126

Reaktionsgleichung

Reaktionsgleichung von HRID 733126
Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][C:12]([CH3:24])([CH3:23])[C:13](=O)[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)(=O)C>[Br:2][C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:12]([CH3:11])([CH3:23])[CH3:24])=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 337573-Bromophenylhydrazine hydrochlorideHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoate

Produkt 1

HCID 57428253ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylateAusbeute 76,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 3-bromophenylhydrazine hydrochloride (0.5 g, 2.2 mmol) and ethyl 5,5-dimethyl-2,4-dioxohexanoate (0.54 g, 2.68 mmol) in acetic acid (10 ml) was refluxed for 16 hours. The reaction was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated bicarbonate and brine, and dried over sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (4.8:0.2 hexanes/ethyl acetate) to give ethyl 1-(3-bromophenyl)-5-tert-butyl-1H-pyrazole-3-carboxylate (0.59 g, 74%) as a syrup.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water, saturated bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by column chromatography (4.8:0.2 hexanes/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-610ff5fafba24af88484ecb8caab413b
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589116B2

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