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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 42013Erstellt: 23. Oktober 2026

Dichloromethane → 5-Bromo-2-(3-methoxyphenyl)pyridine

https://huagongshe.com/de/reaction/42013

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDichloromethaneHCID 6344—
EduktCesium carbonateHCID 10796—
Edukt2,5-DibromopyridineHCID 69353—
Edukt(3-Methoxyphenyl)boronic acidHCID 2734370—
Lösungsmittel1,4-Dioxane--water (1/1)HCID 21886435—
Produkt2-Bromo-5-(3-methoxyphenyl)pyridineHCID 15326155—
Produkt5-Bromo-2-(3-methoxyphenyl)pyridineHCID 4975851943%

Reaktionsschritte

In a schlenck tube, a mixture of 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-methoxyphenylboronic acid (2.11 mmol, 0.321 g), PdCl2dppf.DCM (0.21 mmol, 0.172 g), Cs2CO3 (6.33 mmol, 2.063 g) in a dioxane/water 4:1 mixture (14.5 ml) was heated at 100° C. for 14 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 5-bromo-2-(3-methoxyphenyl)pyridine (0.242 g, yield 43%) as major product and 2-bromo-5-(3-methoxyphenyl)pyridine (0.039 g) as minor product.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08536165B2
Quelldatensatzuspto-grants-2013_09
ORD IDord-3d31eae132414104885a110c6a7d5294
Quellennotizuspto-grants-2013_09