Methanol → 2-Chloro-1-(4-fluoro-3-nitrophenyl)ethan-1-one

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Reaction Conditions

Reaction Steps

1-(4-Fluoro-3-nitrophenyl)ethanone (18.4249 g; manufactured by Sigma-Aldrich Co.) was dissolved in CH2Cl2 (400 mL), added with methanol (3.04 mL), followed by replacement with nitrogen gas and cooling to 0° C. To the resulting solution, SO2Cl2-CH2Cl2 solution [109.32 mL; solution obtained by dissolving SO2Cl2 (9.32 mL; manufactured by Wako Pure Chemical Industries, Ltd.) in CH2Cl2 (100 mL)] was added dropwise over 30 minutes, and the mixture was stirred overnight while warming to room temperature. The reaction solution was cooled to 0° C., added with methanol (1.52 mL), and then SO2Cl2-CH2Cl2 solution [64.66 mL; solution obtained by dissolving SO2Cl2 (4.66 mL; manufactured by Wako Pure Chemical Industries, Ltd.) in CH2Cl2 (60 mL)] was added dropwise thereto. While warming to room temperature, the mixture was stirred for 3 hours. The reaction solution was washed once with a saturated aqueous solution of sodium carbonate and once with brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The solidified crystal, which had been obtained during purification of the resulting residue by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=88:12→67:33), was extracted with ethyl acetate, and then filtered. The filtrate was evaporated under reduced pressure, and as a result, the title compound was obtained (6.403 g).

Provenance & Evidence