N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1640226Notes

Reaction equation

HRID 1640226 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>C(O)(=O)C>[Br:20][C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 708519-Phenylcarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 88.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

24.3 g (100 mmol) of 9-phenylcarbazole was put into a 2L Meyer flask, and dissolved in 600 mL of glacial acetic acid. Then, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added, and the solution was stirred for about 12 hours at room temperature. This solution was dropped into 1 L of ice water while stirring. A white solid precipitated was collected by suction filtration, and then washed with water three times. This solid was dissolved in 150 mL of diethyl ether, and the solution was washed with a saturated aqueous solution of sodium bicarbonate and then with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated, and then the residue was dissolved in ca. 50 mL of ethanol. The precipitate formed as a white solid was collected by suction filtration and dried, giving 28.4 g (88% yield) of 3-bromo-9-phenylcarbazole as white powder.

Workup

  1. stirringwhile stirring
  2. customA white solid precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with water three times
  5. dissolutionThis solid was dissolved in 150 mL of diethyl ether
  6. washthe solution was washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dissolutionthe residue was dissolved in ca. 50 mL of ethanol
  11. customThe precipitate formed as a white solid
  12. filtrationwas collected by suction filtration
  13. customdried

Sources & evidence

ORD record
ord-93cc7434599c47a794a79eb18bd8a064
Source dataset
uspto-grants-2012_02
Patent number
US08110980B2

Reaction notes

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