Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Reactant | HCID 86665745 | HCID 86665745 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69671278 | HCID 69671278 | 72.7% |
Reaction Steps
To a mixture of 2-(2,2-dibromovinyl)-4-difluoromethoxyaniline (166 mg), phenylboronic acid (88.5 mg) and potassium phosphate monohydrate (557 mg) was added a mixture of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (11.9 mg), palladium (II) acetate (3.3 mg) and toluene (2.4 mL) at room temperature, and the mixture was stirred at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and then filtered through celite (registered trademark). The filtrate was washed with saturated saline-water (2/1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (91.2 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680120B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-f2f4e1214c014bbb825359302692de7f |
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| Source note | uspto-grants-2014_03 |
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