反応 #90450

反応方程式

KOH

3,6-dibromocarbazole

Epibromohydrin

→

desired product

収率 66.3%

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

収率 66.3%

溶媒

DMF

反応条件

後処理

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature overnight
3. 3
   その他Upon completion, the solution was partitioned between EtOAc and H2O
4. 4
   洗浄The aqueous layer was washed 3× with EtOAc
5. 5
   洗浄the combined organics were washed with saturated aqueous NaCl
6. 6
   乾燥dried over Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The crude residue was recrystallized from EtOAc/Hexane

実験手順

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%).

出典