Dimethylformamide → Ethyl 2-[(3,5-dichloro-6-fluoropyridin-2-yl)oxy]propanoate

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A solution was prepared by dissolving 1.84 grams (0.08 mole) of sodium metal in 140 milliliters of 28 percent ethanol. To this solution was added 14.6 grams (0.08 mole) of 3,5-dichloro-6-fluoro-2-pyridinol. The solution was warmed and 60 milliliters of N,N-dimethylformamide was added thereto. The solution was further heated to remove about 3/4 of the ethanol. To the remaining solution was added 15.5 grams (0.85 mole) of ethyl bromopropionate followed by an additional 40 milliliters of N,N-dimethylformamide. The mixture was refluxed at 118° C. for 20 minutes, cooled and poured into water. The mixture was extracted with hexane and the hexane thereafter removed by evaporation. The residue was distilled under reduced pressure and the ethyl[2-(3,5-dichloro-6-fluoro-2-pyridyloxy)]propionate was recovered as an oil in a yield of 17.7 grams (78.3 percent of theoretical) and had a boiling point at 2.4 millimeters of mercury at 127° C. Upon analysis, the product was found to have carbon, hydrogen, chlorine and nitrogen contents of 42.0, 3.1, 25.1 and 5.2 percent, respectively, as compared with the theoretical contents of 42.6, 3.6, 25.1 and 4.9 percent, respectively, calculated for the above named compound.

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