Sodium Iodide → 2-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl ester

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A mixture of 2-chloro-1-(4-fluoro-phenyl)-ethanone (4.83 g, 28.0 mmol), ethyl acetoacetate sodium salt (4.26 g, 28.0 mmol) and sodium iodide (420 mg, 2.80 mmol) in acetone (50 mL) was refluxed for 1 h; then the solvents were evaporated, the residue was partitioned between EtOAc and 1 M HCl aqueous solution, the organic phase was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, filtered, concentrated, to give a brown liquid, the title product (7.334 g); 1H NMR (200 MHz, CDCl3): δ (ppm)=8.1-7.9 (m, 2H), 7.2-7.1 (m, 2H), 4.22 (q, 2H, J=6.8 Hz), 4.2-4.0 (m, 1H), 3.8-3.4 (m, 2H), 2.44 (s, 3H), 1.30 (t, 3H, J=6.8 Hz).

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