Dimethyl Sulfate → Methyl 2,4-dichloro-3-(1'-methoxyimino-1-(methoxy)methyl)benzoate

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Reaction Steps

A mixture of 16.0 g (0.058 mol) of methyl 2,4-dichloro-3-methoxyaminocarbonylbenzoate and 10.1 g (0.073 mol) of potassium carbonate in 300 ml of dimethylformamide was stirred for 30 minutes at room temperature. 11.0 g (0.087 mol) of dimethyl sulfate were subsequently added dropwise, the mixture was stirred for 12 hours at room temperature, and another 11.0 g of dimethyl sulfate were added. After the mixture had been heated for 6 hours at 60° C., it was cooled and stirred into 2 l of ice-water. Then, the aqueous phase was extracted with ethyl acetate, the combined organic phases were dried and the solvent was distilled off in vacuo. After chromatography of the residue on silica gel (eluant:toluene/ethyl acetate=9/1), 2.0 g of methyl 2,4-dichloro-3-(1'-methoxyimino-1'-(methoxy)methyl)benzoate were obtained.

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