Iodine → 3-iodo-9H-carbazole

HRID 1008658Notes

Reaction equation

HRID 1008658 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[I:14]I.OS(O)(=O)=O.[OH-].[Na+]>C(O)C.CCOC(C)=O.CCCCCC>[I:14][C:3]1[CH:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][CH:8]=[CH:9][CH:10]=3

Participants

8

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 6854CarbazoleHCID 14798Sodium Hydroxide

Product 1

HCID 36780693-iodo-9H-carbazoleYield 140.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

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.

Workup

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

Sources & evidence

ORD record
ord-4017f5970f0b41a1af1bac5700e2c726
Source dataset
uspto-grants-2011_07
Patent number
US07972792B2

Reaction notes

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