Toluene → 3-Bromo-9-phenylcarbazole

HRID 1910369Notes

Reaction equation

HRID 1910369 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

Into a 1000 mL three-neck flask were put 24 g (100 mmol) of 9-phenylcarbazole, 18 g (100 mmol) of N-bromosuccinimide, 450 mL of toluene, and 200 mL of ethyl acetate, and the mixture was stirred for 45 hours at room temperature. This suspending solution was washed with water, and magnesium sulfate was added therein, so that moisture was removed. Then, the suspending solution was filtered to provide a filtrate was obtained. The obtained filtrate was concentrated and dried, whereby 32 g of a caramel-like solid of 3-bromo-9-phenyl-9H-carbazole, which was the object of the synthesis, was obtained in a yield of 99% (synthesis scheme (a-6)).

Workup

  1. customInto a 1000 mL three-neck flask were put
  2. washThis suspending solution was washed with water, and magnesium sulfate
  3. additionwas added
  4. customso that moisture was removed
  5. filtrationThen, the suspending solution was filtered
  6. customto provide a filtrate
  7. customwas obtained
  8. concentrationThe obtained filtrate was concentrated
  9. customdried
  10. customthe object of the synthesis
  11. customwas obtained in a yield of 99% (synthesis scheme (a-6))

Sources & evidence

ORD record
ord-a2acd80b7d8f4e3dbd53939be04495d8
Source dataset
uspto-grants-2013_12
Patent number
US08603644B2

Reaction notes

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