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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1059965Generated: October 26, 2026

Sodium Carbonate → 4-(4-Methoxypyridin-2-yl)-chlorobenzene

https://huagongshe.com/reaction/1059965

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant4-Chlorophenylboronic acidHCID 74299—
Reactant2-Bromo-4-methoxypyridineHCID 4738484—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
Product4-(4-Methoxypyridin-2-yl)-chlorobenzeneHCID 1863101572.9%

Reaction Conditions

Temperature80 °C

Reaction Steps

To a suspension of 2-bromo-4-methoxypyridine (1.21 g), 4-chlorophenylboronic acid (1.21 g) and tetrakis(triphenylphosphine)-palladium (372 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (7.74 ml). The mixture was stirred at 80° C. for 12 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. 2-Propanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-chlorobenzene (1.03 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06521643B1
Source datasetuspto-grants-2003_02
ORD IDord-7b4452f4ded145f882779aa1ceb51230
Source noteuspto-grants-2003_02