N-Iodosuccinimide → 9-([1,1'-Biphenyl]-4-yl)-3-iodo-9H-carbazole

HRID 1993089Notes

Reaction equation

HRID 1993089 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([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:3][CH:2]=1.[I:26]N1C(=O)CCC1=O>C(O)(=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[I:26][C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:4]3[CH:5]=[CH:6][C:1]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:2][CH:3]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

6

Reactant 2

HCID 120273N-IodosuccinimideHCID 4128979-(4-biphenylyl)carbazole

Product 1

HCID 591329069-([1,1'-Biphenyl]-4-yl)-3-iodo-9H-carbazoleYield 98.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.2 g (10 mmol) of 9-(4-biphenylyl)carbazole was dissolved in a mixed solution of 200 mL of glacial acetic acid, 200 mL of toluene, and 50 mL of ethyl acetate. 2.3 g (10 mmol) of N-iodosuccinimide was slowly added thereto. The mixture was stirred overnight (for about 24 hours) and then washed with water, a sodium thiosulfate water solution, and a saturated sodium chloride solution. Magnesium sulfate was added thereto to remove water and filtered to obtain a filtrate. The filtrate was concentrated, mixed with acetone and hexane, and then recrystallized with ultrasonic wave. This was filtered to obtain a residue. The residue was collected and dried. 4.4 g (yield: 98%) of 3-iodo-9-(4-biphenylyl)carbazole, which was beige powder, was obtained.

Workup

  1. washwashed with water
  2. additionMagnesium sulfate was added
  3. customto remove water
  4. filtrationfiltered
  5. customto obtain a filtrate
  6. concentrationThe filtrate was concentrated
  7. additionmixed with acetone and hexane
  8. customrecrystallized with ultrasonic wave
  9. filtrationThis was filtered
  10. customto obtain a residue
  11. customThe residue was collected
  12. customdried

Sources & evidence

ORD record
ord-b31f760a84424345876e9bcb69486b85
Source dataset
uspto-grants-2010_01
Patent number
US07649197B2

Reaction notes

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