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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 593277Generated: October 29, 2026

Sodium Carbonate → 2-Chloro-4-(2-methoxyphenyl)pyridine

https://huagongshe.com/reaction/593277

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant2-Methoxyphenylboronic acidHCID 2733958—
Reactant4-Bromo-2-chloropyridineHCID 3847770—
CatalystHCID 178418476HCID 178418476—
SolventDimethoxyethane ethanol waterHCID 86587095—
Product2-Chloro-4-(2-methoxyphenyl)pyridineHCID 5843261162.4%

Reaction Conditions

Temperature125 °C

Reaction Steps

To a solution of 4-bromo-2-chloro-pyridine (1.5 g, 7.8 mmol) in DME/water/EtOH 5:1:1 (20 mL) was added (2-methoxyphenyl)boronic acid (1.49 g, 9.8 mmol), Pd(PPh3)2Cl2 (112 mg, 0.16 mmol), and Na2CO3 (1.65 g, 15.6 mmol). The mixture was heated at 125° C. for 90 minutes in a microwave oven. It was concentrated under reduced pressure, and the residue was purified by flash chromatography (silica gel, cHex/EtOAc 100:0 to 80:20) to give the title compound A1 (1.07 g, 62%). MS (ES) C12H10ClNO requires: 219. found: 220 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09242937B2
Source datasetuspto-grants-2016_01
ORD IDord-70dd4265c19847c58a7bdafc0b21f239
Source noteuspto-grants-2016_01