Methyl Ethyl Ketone → 5-Bromo-2,3-dimethyl-1H-indole

HRID 62145

Reaktionsgleichung

Reaktionsgleichung von HRID 62145
[CH3:1][C:2](=O)[CH2:3][CH3:4].Cl.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1>CCO>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:14][C:3]([CH3:4])=[C:2]2[CH3:1]

Komponenten

4

Edukt 2

HCID 6569Methyl Ethyl KetoneHCID 121574-Bromophenylhydrazine hydrochloride

Produkt 1

HCID 127930975-Bromo-2,3-dimethyl-1H-indoleAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL). The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 22 h
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and 1N HCl
  5. washThe organic layer was washed with H2O and saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fc7c7158f45b40b885208137dfb9ea7b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446022B2

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