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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 717264Generated: October 30, 2026

Water → Methyl 5-methyl-2-(pyridin-4-yl)benzoate

https://huagongshe.com/reaction/717264

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
Reactant(Pyridin-4-yl)boronic acidHCID 2734379—
ReactantMethyl 2-bromo-5-methylbenzoateHCID 15110996—
CatalystHCID 178418397HCID 178418397—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
ProductMethyl 5-methyl-2-(pyridin-4-yl)benzoateHCID 8668084148.5%

Reaction Steps

A mixture of methyl 2-bromo-5-methylbenzoate (5.2 g), pyridine-4-boronic acid (4.2 g), sodium carbonate (4.8 g), tetrakis(triphenylphosphine)palladium(0) (1.3 g), water (10 mL) and DME (50 mL) was heated under reflux overnight under a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, and filtered through silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.5 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09193709B2
Source datasetuspto-grants-2015_11
ORD IDord-c7cfb6ccc3484f48b55fc714b1081eb0
Source noteuspto-grants-2015_11