Water → 3-Bromo-9-ethylcarbazole

HRID 452356Notes

Reaction equation

HRID 452356 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].[Br:16]N1C(=O)CCC1=O.O>CN(C=O)C>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([Br:16])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6836N-ethyl carbazoleHCID 67184N-bromobutanimide

Product 1

HCID 6210803-Bromo-9-ethylcarbazoleYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5.00 g of N-ethylcarbazole was dissolved in 130 ml of dehydrated DMF in a flask whose atmosphere was replaced with argon. This solution was cooled to 0° C., 4.60 g of N-bromosuccinimide was charged as 5 divided fractions for 3 hours. After raising the temperature to room temperature and stirring for 12 hours, the reaction liquid was thrown into iced water and filtrated. The residue was washed with water and methanol, and dried under reduced-pressure to give 6.28 g crude product. It was purified with silica gel column chromatography (eluent: cyclohexane containing 0.1% triethylamine), and 5.68 g of N-ethyl-3-bromo carbazole was obtained.

Workup

  1. temperatureAfter raising the temperature to room temperature
  2. customthe reaction liquid
  3. filtrationfiltrated
  4. washThe residue was washed with water and methanol
  5. customdried under reduced-pressure
  6. customto give 6.28 g crude product
  7. customIt was purified with silica gel column chromatography (eluent: cyclohexane containing 0.1% triethylamine)

Sources & evidence

ORD record
ord-5031bac2e15d485fb802d4bda36cafae
Source dataset
uspto-grants-2013_07
Patent number
US08492007B2

Reaction notes

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