Thionyl Chloride → 2-Thiophenecarboxylic acid, 5-(chloromethyl)-, methyl ester

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Reaction Steps

To a solution of methyl 5-(hydroxymethyl)thiophene-2-carboxylate (1.440 g, 8.362 mmol) in anhydrous chloroform (7.5 ml) was added dropwise thionyl chloride (3.62 ml, 50.17 mmol) at 0° C. After stirring at room temperature for 1.5 hrs, the mixture was concentrated under reduced pressure. The residue was dissolved in anhydrous chloroform (10 ml), and the mixture was concentrated again under reduced pressure. This operation was repeated 3 times to remove thionyl chloride azeotropically. The residue was dried under reduced pressure to give crude methyl 5-(chloromethyl)thiophene-2-carboxylate (1.782 g) as a brown oil.

Provenance & Evidence