Carbazole → 9-(4-Bromophenyl)carbazole

HRID 1895845Notes

Reaction equation

HRID 1895845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH:9]1[C:21]2[NH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]=2[CH:12]=[CH:11][CH:10]=1>CN(C)C(=O)C.[Cu-]=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:20]2[C:21]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]3[C:19]2=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6854CarbazoleHCID 115221-Bromo-4-iodobenzene

Product 1

HCID 223613909-(4-Bromophenyl)carbazole

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 31374DimethylacetamideSolvent

Procedure

9-(4-bromophenyl) carbazole was prepared through the Ullmann Reaction following the procedures reported in the literature (Macromolecules 2004, 37, 5531-5537). Briefly, a mixture of 1-bromo-4-iodobenzene (2.83 g, 10 mmol), copper (I) oxide (2.86 g, 20 mmol) and carbazole (0.84 g, 5 mmol) in 10 ml N,N-dimethylacetamide (DMAC) was heated to reflux in an oil bath for 24 h under N2 atmosphere. The reaction mixture was cooled to room temperature and then filtered to remove excess copper complex. The filtrate was evaporated to dryness and went through silica gel column to give product, yielding 1.22 g (76%). 1H NMR (400 MHz, CDCl3): δ(ppm) 8.132-8.122 (d, J=8.0 Hz, 2H), 7.715-7.695 (t, J=8.0 Hz, 2H), 7.476-7.247 (m, 8H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux in an oil bath for 24 h under N2 atmosphere
  3. filtrationfiltered
  4. customto remove excess copper complex
  5. customThe filtrate was evaporated to dryness
  6. customto give product
  7. customyielding 1.22 g (76%)

Sources & evidence

ORD record
ord-25d03e5eaafc4f9a8cf638cf00e18008
Source dataset
uspto-grants-2013_08
Patent number
US08518559B2

Reaction notes

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