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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2425800Generated: October 28, 2026

Toluene → 5-Bromo-2,3'-bipyridine

https://huagongshe.com/reaction/2425800

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant2,5-DibromopyridineHCID 69353—
Reactant3-Pyridinylboronic acidHCID 2734378—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
SolventWaterHCID 962—
Product5-Bromo-2,3'-bipyridineHCID 1139067770.6%

Reaction Steps

Into a 1 l flask, 20 g of 3-pyridine boronic acid, 50 g of 2,5-dibromopyridine, 5.5 g of Pd(PPh3)4, 33.9 g of sodium carbonate, 500 ml of toluene, 150 ml of ethanol, and 150 ml of pure water were put, and the solution was stirred at reflux temperature for 3.5 hours. After heating, the reaction liquid was cooled to room temperature and the organic layer was extracted. The organic layer was concentrated in an evaporator, the concentrates were purified by column chromatography, then, recrystallized in heptane, and thus 27 g of 5-bromo-2,3′-bipyridine was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07964293B2
Source datasetuspto-grants-2011_06
ORD IDord-ee080108e90d41d4a6513a5bb5de9243
Source noteuspto-grants-2011_06