반응 #90450

반응 방정식

KOH

3,6-dibromocarbazole

Epibromohydrin

→

desired product

수율 66.3%

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

수율 66.3%

용매

DMF

반응 조건

후처리

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature overnight
3. 3
   기타Upon completion, the solution was partitioned between EtOAc and H2O
4. 4
   세척The aqueous layer was washed 3× with EtOAc
5. 5
   세척the combined organics were washed with saturated aqueous NaCl
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude residue was recrystallized from EtOAc/Hexane

실험 절차

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%).

출처