Toluene → 3-Bromo-9-phenylcarbazole

HRID 1805968Notes

Reaction equation

HRID 1805968 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 magnesium sulfate was added thereto, so that moisture was removed. This suspension was filtered, and the obtained filtrate was concentrated and dried. The amount and yield of a solid, which was the substance to be produced, were 32 g and 99%, respectively.

Workup

  1. washThis suspension was washed with water, and magnesium sulfate
  2. additionwas added
  3. customso that moisture was removed
  4. filtrationThis suspension was filtered
  5. concentrationthe obtained filtrate was concentrated
  6. customdried
  7. customto be produced

Sources & evidence

ORD record
ord-7155b8c9ddf84e64934e55d74421344b
Source dataset
uspto-grants-2013_01
Patent number
US08354542B2

Reaction notes

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