N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1942978Notes

Reaction equation

HRID 1942978 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%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

First, 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 mL of glacial acetic acid, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added therein, and the mixture was stirred at room temperature for 18 hours. This reaction solution was dripped to 1 L of ice water while being stirred, and a white solid which was precipitated was washed with water three times. The obtained solid was dissolved in 150 mL of diethyl ether and washed with a saturated sodium hydrogen-carbonate aqueous solution and water. After being washed, an organic layer was dried with magnesium sulfate. After filtration, the filtrate was concentrated. Thereafter, approximately 50 mL of methanol was added to an obtained solid, and the solid was irradiated with ultrasonic waves to be uniformly dissolved. This solution was left at rest, and a white precipitate was obtained. This precipitate was collected by filtration and dried; thus, 28.4 g of a white powder of 3-bromo-9-phenylcarbazole that was an object was obtained (yield: 88%).

Workup

  1. stirringwhile being stirred
  2. customa white solid which was precipitated
  3. washwas washed with water three times
  4. dissolutionThe obtained solid was dissolved in 150 mL of diethyl ether
  5. washwashed with a saturated sodium hydrogen-carbonate aqueous solution and water
  6. washAfter being washed
  7. dry with materialan organic layer was dried with magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated
  10. additionThereafter, approximately 50 mL of methanol was added to an obtained solid
  11. customthe solid was irradiated with ultrasonic waves
  12. dissolutionto be uniformly dissolved
  13. waitThis solution was left at rest
  14. customa white precipitate was obtained
  15. filtrationThis precipitate was collected by filtration
  16. customdried
  17. customwas obtained (yield: 88%)

Sources & evidence

ORD record
ord-2997310a8d054e6f82b1b8be07172bba
Source dataset
uspto-grants-2013_03
Patent number
US08389735B2

Reaction notes

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