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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1479509Erstellt: 26. Oktober 2026

Triethylamine → 5-(Benzyloxy)-3-bromopicolinonitrile

https://huagongshe.com/reaction/1479509

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
EduktTrimethylsilyl cyanideHCID 82115—
Edukt3-(benzyloxy)-5-bromopyridine N-oxideHCID 58213489—
LösungsmittelAcetonitrileHCID 6342—
Produkt5-(Benzyloxy)-3-bromopicolinonitrileHCID 67117707—

Reaktionsbedingungen

Temperatur100 °C

Reaktionsschritte

To a solution of 53-(benzyloxy)-5-bromopyridine 1-oxide (from step 2) (1.0 eq.) in acetonitrile (0.2 M) was added trimethylsilyl cyanide (TMSCN) (4.0 eq.) and triethylamine (3.0 eq.). The reaction was heated at 100° C. overnight. After cooling to room temperature, the solvent was concentrated en vacuo, and the residue was purified by a COMBIFLASH® system (ISCO) using 0-40% ethyl acetate in hexane to give a mixture of two benzoxy regioisomers, one of which was the desired product. The mixture was carried onto the next step without further purification.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09408907B2
Quelldatensatzuspto-grants-2016_08
ORD IDord-07f31cbe7b804a029297f3acc9927f3f
Quellennotizuspto-grants-2016_08