1-Bromo-2-methylpropane → 2-bromo-9-isobutyl-9H-carbazole

HRID 1022358Notes

Reaction equation

HRID 1022358 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.[H-].[Na+].[CH2:17](Br)[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 127170892-Bromo-9H-carbazole

Product 1

HCID 595003092-bromo-9-isobutyl-9H-carbazoleYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-bromo-9H-carbazole (4.1 g, 16.74 mmol) was dissolved in DMF. To the stirred solution was slowly added NaH (1.8 g, 75.5 mmol) in 3 portions. Isobutylbromide (4.8 mL, 43.2 mmol) was added to the stirred slurry and after waiting for 20 minute, warmed up to 60° C. for 4 h. Reaction mixture was cooled to room temperature and carefully quenched with drop wise addition of saturated NH4Cl solution. Content was then partitioned in brine and ethylacetate. Organic layer was dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was flashed over silica gel with 10% ethylacetate/hexane. Final product (4.45 g, 14.8 mmol) was isolated as white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customcarefully quenched with drop wise addition of saturated NH4Cl solution
  4. customContent was then partitioned in brine
  5. dry with materialOrganic layer was dried over anhydrous Na2SO4
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-70cd3d998aef4df78f0c7b57179869aa
Source dataset
uspto-grants-2014_05
Patent number
US08722205B2

Reaction notes

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