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ChemicalBook CAS DataBase List ETHYL 2-BROMOISONICOTINATE

ETHYL 2-BROMOISONICOTINATE synthesis

4synthesis methods
-

Yield: 79%

Reaction Conditions:

with sulfuric acid for 3 h;Schlenk technique;Inert atmosphere;Reflux;

Steps:

Ethyl 2-bromoisonicotinate (10c)
A 8 mL Schlenk tube was flushed with nitrogen and charged with 250 mg (1.24 mmol, 1.00 eq) 4-bromopyridine-4-carboxylic acid suspended in 1.0 mL EtOH. After adding 200 μL (3.71 mmol, 3.00 eq)conc. H2SO4 the suspension was heated under reflux for 3 h. TLC analysis (CH/EtOAc 3:1) indicatedfull conversion of the starting material. The mixture was hydrolyzed with 5 mL sat. aqueous NaHCO3solution and extracted with EtOAc (2 x 10 mL). The combined organic layers were dried over MgSO4and the solvent was removed under reduced pressure. Drying in high vacuum and storage in the fridgeovernight yielded the pure product. (79 % yield, 225 mg yellow solid).

References:

Breinbauer, Rolf;Doler, Carina;Fuchs, Elisabeth;Grabner, Gernot F.;Mayer, Nicole;Melcher, Michaela-Christina;Migglautsch, Anna K.;Romauch, Matthias;Schweiger, Martina;Zechner, Rudolf;Zimmermann, Robert [Bioorganic and medicinal chemistry,2020,vol. 28,# 16] Location in patent:supporting information

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