N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1261632Notes

Reaction equation

HRID 1261632 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 into 600 mL of glacial acetic acid, and 17.8 g (100 mmol) of N-bromosuccinimide was slowly added thereto, which was followed by stirring at room temperature for about 15 hours. This glacial acetic acid solution was dropped to 1 L of ice water while being stirred, and a white solid which was precipitated was collected by suction filtration and washed with water three times. The solid was dissolved into 150 mL of diethyl ether, and the solution was washed with a saturated sodium hydrogencarbonate aqueous solution and water. The organic layer was dried with magnesium sulfate. After filtration, the obtained filtrate was concentrated, and about 50 mL of methanol was added thereto to homogeneously dissolve the residue. This solution was left at rest, and a white solid was precipitated. This solid was collected and dried, giving 28.4 g of a white powder of 3-bromo-9-phenylcarbazole in the yield of 88%.

Workup

  1. additionwas slowly added
  2. stirringwhile being stirred
  3. customa white solid which was precipitated
  4. filtrationwas collected by suction filtration
  5. washwashed with water three times
  6. dissolutionThe solid was dissolved into 150 mL of diethyl ether
  7. washthe solution was washed with a saturated sodium hydrogencarbonate aqueous solution and water
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationAfter filtration
  10. concentrationthe obtained filtrate was concentrated
  11. additionabout 50 mL of methanol was added
  12. dissolutionto homogeneously dissolve the residue
  13. waitThis solution was left at rest
  14. customa white solid was precipitated
  15. customThis solid was collected
  16. customdried

Sources & evidence

ORD record
ord-08680cc9c1074ec1b3c54d67462891e8
Source dataset
uspto-grants-2013_06
Patent number
US08471017B2

Reaction notes

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