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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 62842Generated: October 25, 2026

Methyl Acrylate → (E)-3-(4-benzyloxy-3-fluoro-phenyl)-acrylic acid methyl ester

https://huagongshe.com/reaction/62842

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl AcrylateHCID 7294—
Reactant1-(Benzyloxy)-4-bromo-2-fluorobenzeneHCID 18757491—
ReactantTri-t-butylphosphine fluoroborateHCID 44558591—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Product(E)-3-(4-benzyloxy-3-fluoro-phenyl)-acrylic acid methyl esterHCID 9011829622%

Reaction Conditions

Temperature100 °C

Reaction Steps

1-Benzyloxy-4-bromo-2-fluoro-benzene (1.62 g, 5.7 mmol) obtained in Step A was added with methyl acrylate (1 mL), 1,4-dioxane (19 mL), Pd2(dba)3(0.1 g, 0.11 mmol), TEA (1.6 mL, 11.4 mmol) and tri-t-butylphosphine tetrafluoroborate (0.16 g, 0.57 mmol), and the mixture was stirred at 100° C. for 6 hours. The reactant was filtered by using celite, and the filtrate was washed with EtOAc and purified by column chromatography to obtain the title compound (0.37 g, 22%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09447044B2
Source datasetuspto-grants-2016_09
ORD IDord-2b392dbbc5af4db7ac645857e703b8bf
Source noteuspto-grants-2016_09