Toluene → 3-Bromo-9-phenylcarbazole

HRID 1895851Notes

Reaction equation

HRID 1895851 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.C1(C)C=CC=CC=1>C(OCC)(=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

5

Reactant 3

HCID 1140TolueneHCID 67184N-bromobutanimideHCID 708519-Phenylcarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1000 mL conical flask were added 24 g (100 mmol) of 9-phenyl-9H-carbazole, 18 g (100 mmol) of N-bromo succinimide, 450 mL of toluene, and 200 mL of ethyl acetate, and this solution was stirred at room temperature for 45 hours. After the stirring, the obtained mixture was washed with water, and then magnesium sulfate was added therein for drying. When this mixture was filtered and the obtained filtrate was concentrated and dried, 32 g of a brown oily substance of 3-bromo-9-phenylcarbazole, which was the object of the synthesis, was obtained in a yield of 99% (synthesis scheme (X-6)).

Workup

  1. washAfter the stirring, the obtained mixture was washed with water
  2. additionmagnesium sulfate was added
  3. customfor drying
  4. filtrationWhen this mixture was filtered
  5. concentrationthe obtained filtrate was concentrated
  6. customdried
  7. customthe object of the synthesis
  8. customwas obtained in a yield of 99% (synthesis scheme (X-6))

Sources & evidence

ORD record
ord-5e2fa1772e284343b2c795eae78c9737
Source dataset
uspto-grants-2013_08
Patent number
US08518492B2

Reaction notes

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