Hydrochloric Acid → 2-Chloro-5-methylthiophene-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-chloro-3-thiophenecarboxylic acid (2.41 g) was dissolved in tetrahydrofuran (50 ml), and the mixture was cooled to -78° C. N-Butyllithium (1.6M in hexane, 14 ml) was slowly added dropwise. The mixture was stirred at -78° C. for 1 hour, and iodomethane (1.4 ml) was added dropwise. The reaction mixture was warmed to room temperature, stirred at room temperature for 15 hours, poured into water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2-chloro-5-methyl-3-thiophenecarboxylic acid (1.7 g) as crystals.

Provenance & Evidence