p-Fluoronitrobenzene → Diethyl methyl(4-nitrophenyl)propanedioate

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Reaction Steps

1.7 g sodium hydride (60% in mineral oil) are suspended in 10 ml dimethylsulfoxide at 0° C. The a solution of 6.4 ml diethyl 2-methylmalonate in 10 ml dimethylsulfoxide is added dropwise. The mixture is stirred for 30 minutes and then diluted with 20 ml dimethylsulfoxide. After stirring for further 2 hours a solution of 5 g 4-fluoronitrobenzene is added dropwise. The mixture is stirred for 12 hours while warming to room temperature. Then it is partitioned between icewater and ethylacetate. The aqueous phase is twice extracted with ethylacetate and the combined organic phases are washed with brine. After drying with magnesium sulphate the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethylacetate 90:10 to 50:50).

Provenance & Evidence