Diethyl Malonate → Diethyl 2-(4-nitrophenyl)malonate

Participants

Reaction Steps

To a solution of diethyl malonate (320 mg, 2 mmol) in tetrahydrofuran (15 ml) was added a solution of potassium tert-butoxide in tetrahydrofuran (1 M, 2.2 ml, 2.2 mmol). After stirring for 10 minutes, 4-bromonitrobenzene (404 mg, 2 mmol) was added. After stirring for 12 hours, the reaction was quenched by addition of saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl acetate (2×50 ml). The combined extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide crude 2-(4-nitro-phenyl)-malonic acid diethyl ester.

Provenance & Evidence