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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 931855Generated: November 1, 2026

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

https://huagongshe.com/reaction/931855

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant1-Bromo-4-hexylbenzeneHCID 598186—
Reactant2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 11155794—
Reactant4-Chloro-2-cyclohexyl-1-ethynylbenzeneHCID 72942933—
CatalystBis(acetonitrile)dichloropalladiumHCID 6093782—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product4-Chloro-2-cyclohexyl-1-p-tolylethynylbenzeneHCID 67043365—

Reaction Conditions

Temperature100 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09296948B2
Source datasetuspto-grants-2016_03
ORD IDord-1f8a4c5b7e8a403db9a8d44ffeff1526
Source noteuspto-grants-2016_03