تفاعل #595389

معادلة التفاعل

KOH

3,6-dibromocarbazole

Epibromohydrin

→

desired product

المردود 66.3%

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

المردود 66.3%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONuntil dissolved
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature overnight
3. 3
   أخرىUpon completion, the solution was partitioned between EtOAc and H2O
4. 4
   غسيلThe aqueous layer was washed 3× with EtOAc
5. 5
   غسيلthe combined organics were washed with saturated aqueous NaCl
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe crude residue was recrystallized from EtOAc/Hexane

الإجراء التجريبي

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%).

المصدر