N-bromobutanimide → 3-Bromo-9-phenylcarbazole

HRID 2361201Notes

Reaction equation

HRID 2361201 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 AcidSolvent2×

Procedure

24.3 g (100 mmol) of N-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 for about 12 hours 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 solution and water. This organic layer was dried with magnesium sulfate. A mixture is filtered and a filtrate was concentrated. When an obtained residue was recrystallized with methanol, 28.4 g of 3-bromo-9-phenylcarbazole that was a target substance and was white powder was obtained in a yield of 88% (Synthesis Scheme (c-1)).

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 solution and water
  5. dry with materialThis organic layer was dried with magnesium sulfate
  6. filtrationA mixture is filtered
  7. concentrationa filtrate was concentrated
  8. customWhen an obtained residue was recrystallized with methanol, 28.4 g of 3-bromo-9-phenylcarbazole that
  9. customwas obtained in a yield of 88% (Synthesis Scheme (c-1))

Sources & evidence

ORD record
ord-92c66a3b2b8e4206a42d6bc3479c58e0
Source dataset
uspto-grants-2014_04
Patent number
US08686628B2

Reaction notes

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