Toluene → 3-Bromo-9-phenylcarbazole

HRID 2061318Notes

Reaction equation

HRID 2061318 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(OC(=O)C)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 Erlenmeyer 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 ethylacetate were added, and the mixture was stirred at room temperature for 45 hours. After the reaction, the resulting mixture was washed with water, and the organic layer is dried with magnesium sulfate. The mixture was filtered, and the resulting filtrate was concentrated to give 32 g of the desired substance 3-bromo-9-phenyl-9H-carbazole in 99% yield. The synthetic scheme of 3-bromo-9-phenyl-9H-carbazole is shown in the scheme (C-1).

Workup

  1. customAfter the reaction
  2. washthe resulting mixture was washed with water
  3. dry with materialthe organic layer is dried with magnesium sulfate
  4. filtrationThe mixture was filtered
  5. concentrationthe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-579d7af1db214a7f8b43e31cc1234caa
Source dataset
uspto-grants-2012_10
Patent number
US08283055B2

Reaction notes

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