Reaktion #90459

Reaktionsgleichung

3,6-Dibromocarbazole

NaH

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

→

desired product

Ausbeute 34.0%

1,3-Bis(3,6-dibromo-9H-carbazol-9-yl)propan-2-ol

Ausbeute 34.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction was stirred at ambient temperature for 24 h
2. 2
   SonstigeUpon consumption of the starting material by TLC
3. 3
   Sonstigethe reaction 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 purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

Vorschrift

3,6-Dibromocarbazole (0.050 g, 0.154 mmol) was dissolved in DMF (1.5 mL) and cooled to 0° C. NaH (60% dispersion in mineral oil, 0.007 g, 0.169 mmol) was added and the reaction was stirred for 45 min at 0° C. 3,6-Dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole (0.059 g, 0.154 mmol) was added and the reaction was stirred at ambient temperature for 24 h. Upon consumption of the starting material by TLC, the reaction 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 purified by chromatography (SiO2, 0-50% EtOAc/Hexane) to afford the desired product (37 mg, 34%).

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