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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1096951Generated: November 2, 2026

Dimethylformamide → Methyl 5-cyano-[1,1'-biphenyl]-3-carboxylate

https://huagongshe.com/reaction/1096951

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylateHCID 57930914—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
ProductMethyl 5-cyano-[1,1'-biphenyl]-3-carboxylateHCID 57346364—

Reaction Conditions

Temperature90 °C

Reaction Steps

Zinc cyanide (1.1 g) and Pd(PPh3)4 (281 mg) were added to a DMF (45 mL) solution of methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate (1.68 g), and stirred at 90° C. for 1 hour and 30 minutes. The reaction liquid was filtered through Celite, the solvent was partly evaporated away, and the residue was diluted with ethyl acetate, aqueous ammonia was added to it, and the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated away. The residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a white powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08138197B2
Source datasetuspto-grants-2012_03
ORD IDord-00e8522431594b2b8ce1b931a8ea608a
Source noteuspto-grants-2012_03