Dimethyl malonate → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

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To a suspension of NaH (60% in mineral oil, 972 mg, 24.3 mmol) in DMSO (16 mL) is added dimethyl malonate (2.78 mL, 24.3 mmol). The mixture is heated at 60° C. for 10 min and then is cooled to room temperature before 4-bromo-1-fluoro-2-nitro-benzene (1.0 mL, 8.1 mmol) is added. The resulting mixture is heated at 60° C. for 3 hr and then is quenched with saturated aqueous NH4Cl solution. The mixture is extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The crude is used without further purification.

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