HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2062783Generated: November 1, 2026
Ethyl Acetate → Methyl 2'-cyano-3-methoxybiphenyl-4-carboxylate
https://huagongshe.com/reaction/2062783
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Cyanophenylboronic acid | HCID 2734610 | — |
| Reactant | Methyl 4-bromo-2-methoxybenzoate | HCID 15128242 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 2'-cyano-3-methoxybiphenyl-4-carboxylate | HCID 67009848 | 35.6% |
Reaction Steps
A suspension of methyl 4-bromo-2-methoxybenzoate (4.9 g), (2-cyanophenyl)boronic acid (5.9 g), Pd(dppf)2Cl2 (0.49 g) and 2M aqueous cesium carbonate solution (20 mL) in tetrahydrofuran (60 mL) was stirred under an argon atmosphere at 70° C. for 3 hr. The mixture was allowed to cool, ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (1.9 g, 35%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08283353B2 |
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| Source dataset | uspto-grants-2012_10 |
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| ORD ID | ord-bc977ca6658d4668ac7342a737cb7a62 |
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| Source note | uspto-grants-2012_10 |
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