Iodine → 3-iodo-9H-carbazole

Temperature

65 °C

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 added in this order, and then an ethanol solution (100 mL) of H2SO4 (1.60 mL, 30.0 mmol) was added thereto. The reaction solution was heated to reflux for one hour at 65° C. Disappearance of the 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 reaction solution. Ethanol was removed, and then the reaction solution was extracted two times with chloroform and 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 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.

1. temperatureThe reaction solution was heated
2. customEthanol was removed
3. extractionthe reaction solution was extracted two times with chloroform
4. washwashed two times with water
5. dry with materialThe organic phase was dried over Na2SO4
6. customthe solvent was removed
7. customThe residue was purified by column chromatography (HexH:AcOEt=4:1)

ORD record

ord-a58ff5c1996b4579a6a102dcd94ce17c

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481714B2