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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 60588Generated: October 25, 2026

1,2-Dimethoxyethane → Methyl 4-fluoro-2-(pyridin-4-yl)benzoate

https://huagongshe.com/reaction/60588

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
Reactant(Pyridin-4-yl)boronic acidHCID 2734379—
ReactantMethyl 2-bromo-4-fluorobenzoateHCID 7210837—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
ProductMethyl 4-fluoro-2-(pyridin-4-yl)benzoateHCID 4631742259.8%

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of methyl 2-bromo-4-fluorobenzoate (1.5 g), pyridine-4-boronic acid (0.95 g), sodium carbonate (1.0 g), tetrakis(triphenylphosphine)palladium(0) (0.22 g), water (1.5 mL) and DME (9.0 mL) was stirred at 120° C. for 1 hr under microwave irradiation. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.89 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440990B2
Source datasetuspto-grants-2016_09
ORD IDord-279aedb3060b49db9ab32e904f7320cc
Source noteuspto-grants-2016_09