N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1361740Notes

Reaction equation

HRID 1361740 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 for about 12 hours at room temperature. This glacial acetic acid solution was dropped into 1 L of ice water while being stirred. 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 with magnesium sulfate, the mixture was filtered, 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 was produced by keeping this solution still. This solid 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 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 with magnesium sulfate
  8. filtrationthe mixture was filtered
  9. concentrationthe filtrate was concentrated
  10. customThus, an oily substance was obtained
  11. customA precipitate of a white solid was produced
  12. filtrationThis solid was collected by suction filtration
  13. customdried

Sources & evidence

ORD record
ord-614413fc6f63470285b1078cbb8a3fd8
Source dataset
uspto-grants-2011_02
Patent number
US07880019B2

Reaction notes

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