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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1983496Generated: October 31, 2026

Water → 4-Fluoro-5-(3-fluoro-benzoyl)-2-methoxy-benzonitrile

https://huagongshe.com/reaction/1983496

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
Reactant(5-Bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanoneHCID 22260993—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Product4-Fluoro-5-(3-fluoro-benzoyl)-2-methoxy-benzonitrileHCID 22261035—

Reaction Conditions

Temperature120 °C

Reaction Steps

A total of 856 mg of (5-bromo-2-fluoro-4-methoxy-phenyl)-(3-fluoro-phenyl)-methanone obtained in Production Example II-1-b was dissolved in 13.1 ml of N,N-dimethylformamide, 185 mg of zinc cyanide, 13.6 mg of tris(dibenzylideneacetone)dipalladium and 17.4 mg of 1,1′-bis(diphenylphosphino)ferrocene were added thereto, and the mixture was stirred at 120° C. in an atmosphere of nitrogen gas for 7 hours. After cooling to room temperature, water was added to the reaction mixture and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:2), to give 203 mg of the title compound as pale yellow crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07541376B2
Source datasetuspto-grants-2009_06
ORD IDord-12408bd1a0e446e6a3e4e14dad55ef99
Source noteuspto-grants-2009_06