Water → 3,6-Di-tert-butyl-9H-carbazole

HRID 1037504Notes

Reaction equation

HRID 1037504 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.Cl[C:15]([CH3:18])([CH3:17])[CH3:16].O>[N+](C)([O-])=O.[Cl-].[Zn+2].[Cl-]>[C:15]([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][C:8]([C:5]([CH3:6])([CH3:13])[CH3:4])=[CH:9][CH:10]=3)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 962WaterHCID 6854CarbazoleHCID 10486tert-BUTYL CHLORIDE2×

Product 1

HCID 154692093,6-Di-tert-butyl-9H-carbazoleYield 45%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6375NitromethaneSolvent

Procedure

To a solution of carbazole (6.6 g, 39.5 mmol) and zinc (II) chloride (16.2 g, 118.8 mmol) in nitromethane (100.0 ml) was added dropwise 2-chloro-2-methylpropane (11.1 g, 120.0 mmol) under nitrogen atmosphere and stirring. The addition of 2-chloro-2-methylpropane was carried out over a 15 minute period. The mixture was stirred at room temperature for 24 hours. Water (100.0 ml) was then added. The product was extracted with dichloromethane (3×60.0 ml). The organic layer was washed with water (3×100.0 ml), and then dried with MgSO4, and dichloromethane was evaporated under vacuum. The product was purified by recrystallization from hot hexane to afford a white product crystal in the amount of 5.0 g (in 45.0% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. extractionThe product was extracted with dichloromethane (3×60.0 ml)
  3. washThe organic layer was washed with water (3×100.0 ml)
  4. dry with materialdried with MgSO4, and dichloromethane
  5. customwas evaporated under vacuum
  6. customThe product was purified by recrystallization from hot hexane
  7. customto afford a white product crystal in the amount of 5.0 g (in 45.0% yield)

Sources & evidence

ORD record
ord-7eab34bbd09f4d1d9c84e2b9f25ba67c
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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