Carbazole → 9-(Butan-2-yl)-9H-carbazole

HRID 1597737Notes

Reaction equation

HRID 1597737 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.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].I[CH:23]([CH2:25][CH3:26])[CH3:24]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH:23]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)([CH2:25][CH3:26])[CH3:24]

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 105592-IodobutaneHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 205526219-(Butan-2-yl)-9H-carbazoleYield 24.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6228DimethylformamideSolvent

Procedure

30 g (179.46 mmol) of carbazole, 71 g of 85% KOH, 40 g of potassium carbonate, 6.0 g of tetra-n-butylammonium hydrogensulfate, 50.0 g (271.7 mmol) of 2-iodobutane and 300 ml of DMF were allowed to react and after treated in the same manner as with Example 7 (1) to obtain 9.66 g of 9-s-butylcarbazole.

Workup

  1. customto react

Sources & evidence

ORD record
ord-4f59987bfe024d109d20984462e93033
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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