Cesium carbonate → 2-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)benzene

HRID 1041832Notes

Reaction equation

HRID 1041832 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[C:4]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:3]=1.C(C1C=CC(C#C)=CC=1)CC.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[C:53]2[C:58](C(C)C)=[CH:57][C:56]([CH:62](C)[CH3:63])=[CH:55][C:54]=2C(C)C)CCCCC1.O1[CH2:79][CH2:78]OCC1>CC#N.CC#N.Cl[Pd]Cl.O>[CH:17]1([C:4]2[CH:3]=[C:2]([C:63]#[C:62][C:56]3[CH:57]=[CH:58][C:53]([CH2:48][CH2:47][CH2:52][CH2:51][CH2:50][CH3:49])=[CH:54][CH:55]=3)[CH:7]=[CH:6][C:5]=2[C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:78][CH3:79])=[CH:14][CH:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27751331-Ethynyl-4-propylbenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 670433654-Chloro-2-cyclohexyl-1-p-tolylethynylbenzene

Product 1

HCID 1236670432-Cyclohexyl-4-(4-hexylphenylethynyl)-1-(4-propylphenylethynyl)benzene

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4.5 g (11.87 mmol) of 10, 1.7 g (11.87 mmol) of 1-n-propyl-4-ethynyl-benzene, 8.5 g (26.12 mmol) of caesium carbonate, 30 mg (0.1 mmol) of bis(acetonitrile)palladium(II) chloride and 170 mg (0.35 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl are dissolved in 35 ml of dioxane under nitrogen and heated at 100° C. overnight. 100 ml of water are added to the cooled solution, and the mixture is extracted twice with methyl t-butyl ether (100 ml). The combined organic phases are washed with water, dried over sodium sulfate and evaporated in vacuo. The residue is purified by column chromatography, giving the title compound 6 as a solid.

Workup

  1. extractionthe mixture is extracted twice with methyl t-butyl ether (100 ml)
  2. washThe combined organic phases are washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-2869e061967748fa8855941452b23efd
Source dataset
uspto-grants-2013_10
Patent number
US08557142B2

Reaction notes

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