Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Heptane | HCID 8900 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Chlorobiphenyl | HCID 16323 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | HCID 59259711 | HCID 59259711 | 90% |
Reaction Steps
To a mixture of 4-chlorobiphenyl (50 mg, 265 μmol) and 1,4-dioxane (2 ml) were added water (0.2 ml), cesium carbonate (259 mg, 795 μmol), potassium cyclopropylmethoxymethyl trifluoroborate (102 mg, 530 mol), palladium (II) acetate (5.95 mg, 27 μmol) and 2-dicycrohexylphospino-2′,6′-dimethoxybiphenyl (21.8 mg, 53.1 μmol). Then, the reaction mixture was stirred at 100° C. (external temperature) for 7 hours and 30 minutes. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, followed by filtration using Celite. The separated organic layer was washed with an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=30:1) to obtain the title compound (57 mg, 239 μmol, 90%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07696347B2 |
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| Source dataset | uspto-grants-2010_04 |
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| ORD ID | ord-ff18346e62c74d9a87fb81ed027478bb |
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| Source note | uspto-grants-2010_04 |
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