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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1688465Generated: November 1, 2026

Toluene → 4'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrile

https://huagongshe.com/reaction/1688465

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant4-Bromo-2-(trifluoromethyl)benzaldehydeHCID 12187218—
Reactant2-Cyano-phenylboric acidHCID 21708089—
CatalystTetrabutylammonium BromideHCID 74236—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventEthyl AcetateHCID 8857—
Product4'-Formyl-3'-(trifluoromethyl)biphenyl-2-carbonitrileHCID 8664402632.7%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4-bromo-2-(trifluoromethyl)benzaldehyde (9 g), 2-cyano-phenylboric acid (9.5 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (2.9 g), tetrabutylammonium bromide (1.15 g), 2M aqueous sodium carbonate solution (30 mL) and toluene (100 mL) was stirred at 100° C. overnight under an argon atmosphere. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (3.2 g, 32%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08148383B2
Source datasetuspto-grants-2012_04
ORD IDord-b989a4bd88244f89afb7f9eaf1404fe0
Source noteuspto-grants-2012_04