N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 2063182Notes

Reaction equation

HRID 2063182 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.CO>[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

5

Reactant 2

HCID 67184N-bromobutanimideHCID 708519-Phenylcarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 88.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

24.3 g (100 mmol) of 9-phenylcarbazole was put into a 2 L Meyer flask, and dissolved in 600 mL of glacial acetic acid. Then, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added thereto, and the solution was stirred at room temperature for about 12 hours. This glacial acetic acid solution was dropped into 1 L of ice water while being stirred. A white solid substance precipitated was collected by suction filtration, and then washed with water three times. This solid substance was dissolved in 150 mL of diethyl ether, and the solution was washed with a saturated sodium hydrogen carbonate aqueous solution and then with water. The organic layer was dried with magnesium sulfate, the mixture was filtered by suction filtration, and the filtrate was concentrated. Thus, an oily substance was obtained. The oily substance was dissolved in about 50 mL of methanol. A precipitate of a white solid substance was produced by keeping this solution still. This solid substance was collected by suction filtration and dried. Then, 28.4 g (88% yield) of 3-bromo-9-phenylcarbazole was obtained as white powder.

Workup

  1. stirringwhile being stirred
  2. customA white solid substance precipitated
  3. filtrationwas collected by suction filtration
  4. washwashed with water three times
  5. dissolutionThis solid substance was dissolved in 150 mL of diethyl ether
  6. washthe solution was washed with a saturated sodium hydrogen carbonate aqueous solution
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationthe mixture was filtered by suction filtration
  9. concentrationthe filtrate was concentrated
  10. customThus, an oily substance was obtained
  11. customA precipitate of a white solid substance was produced
  12. filtrationThis solid substance was collected by suction filtration
  13. customdried

Sources & evidence

ORD record
ord-f7de5fe875af4f448ab94a6b905115f7
Source dataset
uspto-grants-2012_10
Patent number
US08288012B2

Reaction notes

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