Acetic Anhydride → 9-Acetyl-3-bromocarbazole

HRID 403149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403149
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[C:15](OC(=O)C)(=[O:17])[CH3:16]>OS(O)(=O)=O.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:15](=[O:17])[CH3:16])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Komponenten

5

Edukt 2

HCID 7918Acetic AnhydrideHCID 2524463-Bromocarbazole

Produkt 1

HCID 17148799-Acetyl-3-bromocarbazoleAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 3-bromo-9H-carbazole (10.00 g, 40.6 mmol), acetic anhydride (8.30 g, 81 mmol) together with 2 drops of H2SO4 in chloroform (150 mL) was refluxed overnight. After cooling to room temperature, the solution was washed with water. Upon evaporation of the solvent, the crude product was purified by crystallization from hexane/DCM and hexane/EtOAc to yield 1-(3-bromo-9H-carbazol-9-yl)ethanone (6.1 g, 51% yield) as a light yellow solid.

Aufarbeitung

  1. washthe solution was washed with water
  2. customUpon evaporation of the solvent
  3. customthe crude product was purified by crystallization from hexane/DCM and hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-448e779b27c0471baaa8051f1674588c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748012B2

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