Reaction #90450

Reaction equation

KOH

3,6-dibromocarbazole

Epibromohydrin

→

desired product

Yield 66.3%

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

Yield 66.3%

Solvents

DMF

Conditions

Workup

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

Procedure

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%).

Source