Triethylamine → HCID 68547563, compound

Participants

Reaction Steps

A solution of methyl 6-chloro-3-{ [(trifluoromethyl)sulfonyl]oxy}-1-benzothiophene-2-carboxylate (2.0 g, 5.3 mmol) and triethylamine (890 μL, 1.2 eq), in dichloromethane (45 mL) was cooled to −20° C. and methyl thioglycolate(908 μL, 2.5 eq) was added dropwise via syringe pump over 5 h. The reaction was allowed to warm to room temperature overnight. The solution was diluted with water, and ethyl acetate, washed with water and brine, dried, filtered, evaporated, and flash chromatographed (10-20% ethyl acetate/hexanes) to provide methyl 6-chloro-3-[(cyanomethyl)thio]-1-benzothiophene-2-carboxylate (1.01 g, 64%) as a white solid.

Provenance & Evidence