Toluene → 3-Bromo-9-phenylcarbazole

HRID 626605Notes

Reaction equation

HRID 626605 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-phenylcarbazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a 1-L conical flask, 24 g (100 mmol) of 9-phenyl-9H-carbazole, 18 g (100 mmol) of N-bromosuccinimide, 450 mL of toluene, and 200 mL of ethyl acetate were stirred at room temperature for 45 hours. This suspension was washed with water, and then magnesium sulfate was added thereto to remove moisture. This suspension was filtered, and the obtained filtrate was concentrated and dried. The objective substance was obtained as 32 g of a highly viscous oily substance in 99% yield.

Workup

  1. washThis suspension was washed with water
  2. additionmagnesium sulfate was added
  3. customto remove moisture
  4. filtrationThis suspension was filtered
  5. concentrationthe obtained filtrate was concentrated
  6. customdried
  7. customThe objective substance was obtained as 32 g of a highly viscous oily substance in 99% yield

Sources & evidence

ORD record
ord-86bd2e10e00f4826879d92925503f282
Source dataset
uspto-grants-2016_04
Patent number
US09309223B2

Reaction notes

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