Reaktion #90419

Reaktionsgleichung

KOH

3,6-dibromocarbazole

Epibromohydrin

→

desired product

Ausbeute 66.3%

3,6-Dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole

Ausbeute 66.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature overnight
3. 3
   SonstigeUpon completion, the solution was partitioned between EtOAc and H2O
4. 4
   WaschenThe aqueous layer was washed 3× with EtOAc
5. 5
   Waschenthe combined organics were washed with saturated aqueous NaCl
6. 6
   Trocknendried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe crude residue was recrystallized from EtOAc/Hexane

Vorschrift

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%).

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