Reaktion #1095840

Reaktionsgleichung

carbazole

I2

NaOH

H2SO4

→

compound 1

Ausbeute 140.1%

3-Iodocarbazole

Ausbeute 140.1%

Lösungsmittel

ethanol

AcOEt

ethanol

HexH

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeEthanol was removed
2. 2
   Extraktionthe reaction solution was extracted two times with chloroform
3. 3
   WaschenThe extract was washed two times with water
4. 4
   TrocknenThe organic phase was dried over Na2SO4
5. 5
   Sonstigethe solvent was removed
6. 6
   SonstigeThe residue was purified by column chromatography (HexH:AcOEt=4:1)

Vorschrift

To an ethanol solution (500 mL) of carbazole (2.50 g, 15.0 mmol), NaIO4 (0.80 g, 3.75 mmol) and I2 (1.89 g, 7.45 mmol) were sequentially added, and then an ethanol solution (100 mL) of H2SO4 (1.60 mL, 30.0 mmol) was added. The reaction solution was refluxed for one hour at 65° C. The loss of raw materials was confirmed by TLC (HexH:AcOEt=4:1), and an ethanol solution (100 mL) of NaOH (1.4 g) was added thereto to neutralize the system. Ethanol was removed, and then the reaction solution was extracted two times with chloroform. The extract was washed two times with water. The organic phase was dried over Na2SO4, and the solvent was removed. The residue was purified by column chromatography (HexH:AcOEt=4:1), and thus compound 1 (3.06 g, 70%) was obtained as a white powder. Thus, 3,6-diiodocarbazole (0.47 g, 7.5%) was obtained as a white powder.

Quelle