Methyl cyanoacetate → methyl 2-cyano-2-(2-nitrophenyl)acetate

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Reaction Steps

A solution of methyl cyanoacetate (24.75 g; 0.25M) in dimethylformamide (70 ml) was added dropwise over 40 minutes to a stirred suspension of sodium hydride (8.25 g; 0.275M) in dimethylformamide (250 ml) at 0° under nitrogen atmosphere. The solution was stirred for 0.5 h, then a solution of 2-fluoronitrobenzene (17.65 g; 0.125M) in dimethylformamide (70 ml) added. After stirring for 16 h at room temperature, the red solution was poured onto excess brine, and extracted with ether (×6). The aqueous layer was then acidified with hydrochloric acid (5M) until the red colour was discharged. The resultant solution was extracted with ether (×4) and the combined organic extracts washed with brine, dried and evaporated to afford the title compound as a yellow oil (26.7 g; 97%) which slowly solidified.

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