1,10-Phenanthroline → 9-(4'-Bromo-4-biphenylyl)carbazole

HRID 1628371Notes

Reaction equation

HRID 1628371 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[Br:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][C:44](Br)=[CH:43][CH:42]=2)=[CH:37][CH:36]=1>[Cu]I.CN(C=O)C>[Br:34][C:35]1[CH:36]=[CH:37][C:38]([C:41]2[CH:46]=[CH:45][C:44]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)=[CH:43][CH:42]=2)=[CH:39][CH:40]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 6854CarbazoleHCID 71104,4'-DibromobiphenylHCID 11430Potassium Carbonate

Product 1

HCID 588923869-(4'-Bromo-4-biphenylyl)carbazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

5.0 g of 9H-carbazole (3.0 10−2 mol), 0.67 g of CuI (3.2 10−3 mol), 10.0 g of K2CO3 (7.2 10−2 mol), 1.16 g of 1,10 phenanthroline (6.4 10−3 mol), and 9.36 g of 4,4′-dibromobiphenyl (3.0 10−2 mol) are initially introduced. After addition of 200 ml of DMF, the reaction mixture is stirred under reflux for 12 h. After filtration through Celite with suction, it is precipitated using water and filtered off with suction. The solid is dissolved in hot THF and precipitated using ethanol, giving 7.7 g (64%) of clean substance.

Workup

  1. temperatureunder reflux for 12 h
  2. filtrationAfter filtration through Celite with suction, it
  3. customis precipitated
  4. filtrationfiltered off with suction
  5. dissolutionThe solid is dissolved in hot THF
  6. customprecipitated
  7. customgiving 7.7 g (64%) of clean substance

Sources & evidence

ORD record
ord-ed3051104169422280d1bd57ad7e9857
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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