Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 555995Generated: October 30, 2026

Potassium Carbonate → 3-Bromo-5-ethylpyridine

https://huagongshe.com/reaction/555995

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant3,5-DibromopyridineHCID 69369—
ReactantEthylboronic acidHCID 521157—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
CatalystHCID 178418778HCID 178418778—
SolventTetrahydrofuranHCID 8028—
Product3-Bromo-5-ethylpyridineHCID 642804—

Reaction Steps

3,5-dibromo-pyridine (0.4 g, 1.688 mmol), potassium carbonate (0.7 g, 5.064 mmol), [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.138 g, 0.169 mmol), silver(I) oxide (0.902 g, 4.22 mmol), ethyl boronic acid (0.150 g, 2.03 mmol) and THF (8 ml) are mixed together, purged with argon and heated to reflux overnight. After cooling to room temperature the reaction mixture is filtered through Celite® (filter agent) washing with DCM. The DCM is reduced in vacuo and the residue is purified by flash chromatography by loading onto a 20 g silica column eluting with DCM to afford the title compound, [MH+ 185.91 and 187.91].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08053574B2
Source datasetuspto-grants-2011_11
ORD IDord-02fb406c602a4af6b6e2a0b34182214a
Source noteuspto-grants-2011_11