N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 1993084Notes

Reaction equation

HRID 1993084 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

Firstly, 24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 mL of glacial acetic acid, and 17.8 g (100 mmol) of N-bromosuccinimide was slowly added thereto. The mixture was stirred overnight at a room temperature. This glacial acetic acid solution was dropped into 1 L of ice water while stirring it. A precipitated white solid was washed with water three times. This solid was dissolved in 150 mL of diethyl ether, and washed with a saturated sodium hydrogen carbonate water solution and water. This organic phase was dried with magnesium sulfate, and filtered. The obtained filtrate was concentrated. About 50 mL of methanol was added to the obtained residue and uniformly dissolved therein. This solution was left still to precipitate a white solid. This solid was collected and dried to obtain 28.4 g (yield: 88%) of 3-bromo-9-phenylcarbazole, which was white powder.

Workup

  1. stirringwhile stirring it
  2. washA precipitated white solid was washed with water three times
  3. dissolutionThis solid was dissolved in 150 mL of diethyl ether
  4. washwashed with a saturated sodium hydrogen carbonate water solution and water
  5. dry with materialThis organic phase was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe obtained filtrate was concentrated
  8. additionAbout 50 mL of methanol was added to the obtained residue
  9. dissolutionuniformly dissolved
  10. waitThis solution was left still
  11. customto precipitate a white solid
  12. customThis solid was collected
  13. customdried

Sources & evidence

ORD record
ord-104e785ebba5400faf09c4451692831b
Source dataset
uspto-grants-2010_01
Patent number
US07649197B2

Reaction notes

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