Potassium Hydroxide → 3,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazole

HRID 62172

Reaktionsgleichung

Reaktionsgleichung von HRID 62172
[OH-].[K+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH:16]=1)=[CH:13][C:12]([Br:17])=[CH:11][CH:10]=3.[CH2:18]([CH:20]1[O:22][CH2:21]1)Br>CN(C=O)C>[Br:17][C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:18][CH:20]3[CH2:21][O:22]3)[C:7]3[C:15]([C:14]=2[CH:13]=1)=[CH:16][C:4]([Br:3])=[CH:5][CH:6]=3

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 18430EpibromohydrinHCID 2748743,6-Dibromocarbazole

Produkt 1

HCID 27754733,6-dibromo-9-((oxiran-2-yl)methyl)-9H-carbazoleAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following a literature procedure (Asso, V.; Ghilardi, E.; Bertini, S.; Digiacomo, M.; Granchi, C.; Minutolo, F.; Rapposelli, S.; Bortolato, A.; Moro, S. Macchia, M. ChemMedChem, 2008, 3, 1530-1534) powdered KOH (0.103 g, 1.85 mmol) was added to a solution of 3,6-dibromocarbazole (0.500 g, 1.54 mmol) in DMF (1.5 mL) at ambient temperature and stirred for 30 min until dissolved. Epibromohydrin (0.32 mL, 3.8 mmol) was added via syringe and the reaction was stirred at room temperature overnight. Upon completion, the solution was partitioned between EtOAc and H2O. The aqueous layer was washed 3× with EtOAc, and the combined organics were washed with saturated aqueous NaCl, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was recrystallized from EtOAc/Hexane to afford the desired product (389 mg, 66%).

Aufarbeitung

  1. dissolutionuntil dissolved
  2. stirringthe reaction was stirred at room temperature overnight
  3. customUpon completion, the solution was partitioned between EtOAc and H2O
  4. washThe aqueous layer was washed 3× with EtOAc
  5. washthe combined organics were washed with saturated aqueous NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was recrystallized from EtOAc/Hexane

Quellen und Nachweise

ORD-Eintrag
ord-32a255d7c63a48e4a5b9df1859013124
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446042B2

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