Hydrogen Peroxide → 3-iodo-N-ethylcarbazole

HRID 1291975Notes

Reaction equation

HRID 1291975 reaction equation
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[I:16]I.OO.S(=O)(=O)(O)O>O.C(O)(=O)C.O>[I:16][C:7]1[CH:6]=[CH:5][C:4]2[N:3]([CH2:1][CH3:2])[C:15]3[C:10]([C:9]=2[CH:8]=1)=[CH:11][CH:12]=[CH:13][CH:14]=3

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 807IodineHCID 1118Sulfuric AcidHCID 6836N-ethyl carbazole

Product 1

HCID 40733623-iodo-N-ethylcarbazoleYield 126.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

Into 5.0 g (25.6 mmol) of 9-ethylcarbazole, 40 ml of a 9:1 acetic acid-water mixture, 3.3 g (13.0 mmol) of iodine, 2.5 g of a 30% hydrogen peroxide solution, and 1.8 g of 97% sulfuric acid were added, and the mixture was stirred at 60° C for 2 hours. After natural cooling, the mixture was diluted with water and then extracted with toluene. After the toluene layer was concentrated, the residual component was purified with a silica gel column. As a result, 5.3 g of 3-iodo-9-ethylcarbazole was obtained (corresponding to a 65% yield).

Workup

  1. extractionextracted with toluene
  2. concentrationAfter the toluene layer was concentrated
  3. customthe residual component was purified with a silica gel column

Sources & evidence

ORD record
ord-b37ac43a3c0243d18eb0c5bbdba4dfce
Source dataset
uspto-grants-1998_05
Patent number
US05756248

Reaction notes

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