Hydrochloric Acid → Ethyl 5-nitro-1-benzothiophene-2-carboxylate

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Reaction Steps

To a suspension of sodium hydride (60% in mineral oil, 1.3 g, 33.5 mmol) in dimethylformamide (50 mL) was added dropwise ethyl 2-mercaptoacetate (2.95 mL, 27 mmol) at 0° C. under an atmosphere of argon. After stirring at room temperature for 15 minutes, 2-chloro-5-nitrobenzaldehyde was added. The mixture was then stirred at 100° C. for 6 h, cooled to room temperature and poured into hydrochloric acid (250 mL, 1M). The precipitate was filtered off, washed with water (3×50 mL), dried under reduced pressure and recrystallised from ethyl acetate to give the title compound (5.5 g, 82%) as a solid, mp 163° C.

Provenance & Evidence