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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1688821Generated: October 29, 2026

Ethyl Acetate → Ethyl 2'-cyano-2-methoxybiphenyl-4-carboxylate

https://huagongshe.com/reaction/1688821

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantCesium carbonateHCID 10796—
Reactant2-Cyanophenylboronic acidHCID 2734610—
ReactantEthyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoateHCID 22171362—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductEthyl 2'-cyano-2-methoxybiphenyl-4-carboxylateHCID 670083805%

Reaction Conditions

Temperature70 °C

Reaction Steps

A suspension of ethyl 3-methoxy-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (7.0 g), (2-cyanophenyl)boronic acid (5.9 g), Pd(dppf)2Cl2 (0.50 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 (0.28 g, 5%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08148383B2
Source datasetuspto-grants-2012_04
ORD IDord-361f86b95fd2412eaca79537f06ec529
Source noteuspto-grants-2012_04