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Cesium carbonate → 4-Chloro-2-cyclohexyl-1-p-tolylethynylbenzene

HRID 931855
Notes
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Reaction equation

HRID 931855 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=1.Br[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]CCCCC)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>O1CCOCC1.CC#N.CC#N.Cl[Pd]Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[C:4]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 5981861-Bromo-4-hexylbenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 729429334-Chloro-2-cyclohexyl-1-ethynylbenzene

Product 1

HCID 670433654-Chloro-2-cyclohexyl-1-p-tolylethynylbenzene

Reagents, catalysts & solvents 3

HCID 6093782
Bis(acetonitrile)dichloropalladium
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

6.6 g (30.17 mmol) of 9, 7.28 g (30.17 mmol) of 1-bromo-4-hexylbenzene, 21.63 g (66.39 mmol) of caesium carbonate, 78 mg (0.3 mmol) of bis(acetonitrile)palladium(II) chloride and 431 mg (0.9 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl are dissolved in 90 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.

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-1f8a4c5b7e8a403db9a8d44ffeff1526
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296948B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes