Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Tetrahydro-2-(2-propynyloxy)-2H-pyran | HCID 98609 | — |
| Reactant | 5-Bromo-2-fluorotoluene | HCID 123527 | — |
| Catalyst | Bis(acetonitrile)dichloropalladium | HCID 6093782 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 59407505 | HCID 59407505 | — |
Reaction Steps
A mixture of 5-bromo-2-fluorotoluene (10.0 g), cesium carbonate (45.0 g), 2-(2-propynyloxy)tetrahydropyran (11.2 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.51 g), bis(acetonitrile)palladium(II) dichloride (274 mg) and acetonitrile (300 ml) was stirred at 85° C. for 10 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-90:10) to give the object product (8.08 g) as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08129361B2 |
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| Source dataset | uspto-grants-2012_03 |
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| ORD ID | ord-fd9c26909b7c45f0bcee533c8fd599bd |
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| Source note | uspto-grants-2012_03 |
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