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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2194892Generated: November 1, 2026

Sodium Carbonate → 2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

https://huagongshe.com/reaction/2194892

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Chlorophenylboronic acidHCID 2734322—
Reactant2-(4-Bromo-2-fluorophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrileHCID 67445695—
Catalystpalladium acetate PPh3HCID 11554889—
SolventWaterHCID 962—
Solventtert-ButanolHCID 6386—
Product2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrileHCID 67448242—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution 2-(4-bromo-2-fluorophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile (1 eq.) from step 1 and 2-chlorophenylboronic acid (2 eq.) in tert-butanol (0.16M) at room temperature was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 4 eq.). The mixture was stirred at 80° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/Tol (55 to 65%) afforded the desired compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08334308B2
Source datasetuspto-grants-2012_12
ORD IDord-9198a90220414503a96d6151b1a536fc
Source noteuspto-grants-2012_12