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ChemicalBook CAS DataBase List Methyl 6-chloro-5-(trifluoroMethyl)picolinate

Methyl 6-chloro-5-(trifluoroMethyl)picolinate synthesis

3synthesis methods
-

Yield:1211518-35-2 63%

Reaction Conditions:

with trichlorophosphate at 0 - 50;

Steps:

113.c

Oxy-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (2.2 g, 10 mmol) was added in portions to phosphoryl trichloride (CAN 10025-87-3, 10 mL) at 0° C. and the resulting mixture was stirred at 50° C. overnight. Removal of the solvent in vacuo gave a brown oil which was dissolved in ethyl acetate (30 mL) and carefully neutralized with a aqueous solution of sodium carbonate. The mixture was extracted with ethyl acetate (2×30 mL) and the combined organic phase was washed with brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated to give a light-brown solid. The solid was purified by column chromatography (silica gel, 15 g, 3% ethyl acetate in petroleum ether) to give the target compound (1.5 g, 63%) as white solid; MS (EI): m/e=240.0 [M+H]+.

References:

US2012/316147,2012,A1 Location in patent:Page/Page column 77