N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1926176Notes

Reaction equation

HRID 1926176 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 AcidSolvent2×

Procedure

24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 mL of a glacial acetic acid, 17.8 g (100 mmol) of N-bromosuccinimide was gradually added thereto, and the mixture was stirred for approximately 20 hours at a room temperature. This glacial acetic acid solution was dropped into 1 L of ice water while stirring. The precipitated white solid was washed with water three times. This solid was dissolved in 150 mL of diethyl ether and the solution was washed with a saturated aqueous sodium hydrogen carbonate solution and water. An organic layer thereof was dried with magnesium sulfate. The organic layer was filtered, and the obtained filtrate was concentrated, where about approximately 50 mL of methanol was added and dissolved uniformly. The white solid was precipitated by leaving this solution at rest. This solid was recovered and dried, thereby obtaining 28.4 g (yield: 88%) of 3-bromo-9-phenylcarbazole as a white powder.

Workup

  1. stirringwhile stirring
  2. washThe precipitated white solid was washed with water three times
  3. dissolutionThis solid was dissolved in 150 mL of diethyl ether
  4. washthe solution was washed with a saturated aqueous sodium hydrogen carbonate solution and water
  5. dry with materialAn organic layer thereof was dried with magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. concentrationthe obtained filtrate was concentrated
  8. additionwhere about approximately 50 mL of methanol was added
  9. dissolutiondissolved uniformly
  10. customThe white solid was precipitated
  11. customby leaving this solution at rest
  12. customThis solid was recovered
  13. customdried

Sources & evidence

ORD record
ord-9e417c587ab247429a3ffdd238e783db
Source dataset
uspto-grants-2012_05
Patent number
US08178885B2

Reaction notes

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