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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 474575Generated: October 29, 2026

Ethyl Acrylate → Ethyl 4-Cyanocinnamate

https://huagongshe.com/reaction/474575

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcrylateHCID 8821—
ReactantBenzonitrile, 4-bromo-HCID 12162—
CatalystTri-o-tolylphosphineHCID 80271—
Catalystpalladium(II) acetateHCID 167845—
SolventDimethylformamideHCID 6228—
ProductEthyl 4-CyanocinnamateHCID 537349794%

Reaction Conditions

Temperature110 °C

Reaction Steps

To the mixture of 4-bromobenzonitrile (2.6 g, 14.28 mmol), Pd(OAc)2 (0.064 g, 0.286 mmol) and tri-o-tolylphosphine (0.261 g, 0.857 mmol) in dry DMF (20 mL) was added ethyl 2-propenoate (2.282 mL, 21.43 mmol) and TEA (3.98 mL, 28.6 mmol). It was heated at 110° C. for 1 h. Purification via a flash column chromatography then provided the title compound as a white solid (2.7 g, 92% yield). LCMS: rt=3.03 Min, [M+H+]=202.0

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08637536B2
Source datasetuspto-grants-2014_01
ORD IDord-0f495ec27245446ea276ec303b185207
Source noteuspto-grants-2014_01