Reaction #1095840

Reaction equation

carbazole

I2

NaOH

H2SO4

→

compound 1

Yield 140.1%

3-Iodocarbazole

Yield 140.1%

Solvents

ethanol

AcOEt

ethanol

HexH

ethanol

Conditions

Workup

1. 1
   OtherEthanol was removed
2. 2
   Extractionthe reaction solution was extracted two times with chloroform
3. 3
   WashThe extract was washed two times with water
4. 4
   DryingThe organic phase was dried over Na2SO4
5. 5
   Otherthe solvent was removed
6. 6
   OtherThe residue was purified by column chromatography (HexH:AcOEt=4:1)

Procedure

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.

Source