Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester | HCID 11087024 | — |
| Reactant | 4-Chloro-1-ethenyl-2-nitrobenzene | HCID 15150381 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67513886 | HCID 67513886 | — |
Reaction Steps
4-Chloro-1-ethenyl-2-nitrobenzene (1.1406 g, 6.21 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.059 g, 7.46 mmol), 1,1bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.422 g, 0.621 mmol), cesium carbonate (4.25 g, 13.05 mmol) and THF (30 mL) were heated in an 80° C. oil bath overnight. Volatiles were removed under reduced pressure. The pot residue was taken up by dichloromethane and filtered. The filtrate was concentrated in vacuo to afford a dark solid. The resulting solid was purified by flash chromatography (SiO2, Biotage SNAP cartridge, silica gel, 100 g cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated a light orange solid as the titled compound. LCMS calc.=297.10. found=298.10 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221834B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-f21a300043c64f8aa32182b5cf76dd63 |
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| Source note | uspto-grants-2015_12 |
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