5-Bromo-2-iodo-4-picoline synthesis

Yield:-

Reaction Conditions:

with acetyl chloride;sodium iodide in acetonitrile at 20; for 3 h;Inert atmosphere;

Steps:

17.A
To a solution of 2,5-dibromo-4-methylpyridine (2 g) in acetonitrile (40 ml) at room temperature under argon were added sodium iodide (4.8 g) then acetyl chloride (0.94 g). After 3 hours stirring at room temperature the white solid formed was filtered off and the filtrate was neutralized with aqueous saturated solution of sodium hydrogenocarbonate. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate / cyclohexane) to afford the title product as a brown solid (2.04 g). 1H-NMR (CDC1₃, 400 MHz): 8.40 (s, 1H), 7.60 (s, 1H), 2.30 (s, 3H),

References:

SYNGENTA PARTICIPATIONS AG;CASSAYRE, Jérôme Yves;RENOLD, Peter;EL QACEMI, Myriem;PITTERNA, Thomas;TOUEG, Julie Clementine WO2011/67272, 2011, A1 Location in patent:Page/Page column 76