Toluene → HCID 66744100, compound

HRID 535229Notes

Reaction equation

HRID 535229 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:31]3[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=3)[C:34]#[N:35])[C:22]3[C:27]([C:28]=2[CH:29]=1)=[CH:26][C:25](Br)=[CH:24][CH:23]=3.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.[C:52]1(C)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].O>[C:7]1([C:17]2[CH:18]=[CH:19][C:20]3[N:21]([C:31]4[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=4)[C:34]#[N:35])[C:22]4[C:27]([C:28]=3[CH:29]=2)=[CH:26][C:25]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[CH:24][CH:23]=4)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 58131159HCID 58131159, compound

Product 1

HCID 66744100HCID 66744100, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

In a 250 ml two-neck flask, 30 ml of toluene, 12 ml of water, 0.5 g (0.4 mmol) of Pd(pph3)4, 3.3 g (24 mmol) of potassium carbonate, 1.5 g (12.3 mmol) of phenylboronic acid, 2 g (4.7 mmol) of 3-(3,6-dibromo-9H-carbazol-9-yl)benzonitrile, 20 ml (1 mmol) of PtBu3, and a stir bar were added. The reaction was carried out with stirring and reflux under a nitrogen atmosphere for 24 hours. After the completion of reaction, an extraction was conducted with dichloromethane and water, and the resultant organic layer was further concentrated to obtain a solid product, which was purified by column chromatography to obtain a white solid product of 3-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (yield: 69.8%).

Workup

  1. temperaturereflux under a nitrogen atmosphere for 24 hours
  2. customAfter the completion of reaction
  3. extractionan extraction
  4. concentrationthe resultant organic layer was further concentrated
  5. customto obtain a solid product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-1a037ef3cfc34d82a98f3082bda1e60f
Source dataset
uspto-grants-2014_10
Patent number
US08859113B2

Reaction notes

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