Hydrochloric Acid → 1522107-19-2

Participants

Reaction Conditions

Reaction Steps

To solution of 2-isobutylthiophene (743 mg, 5.30 mmol) in 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (2.3 mL, 2.5 M in hexanes) dropwise. The resulting solution was stirred for 20 minutes at −78° C. Bromine (0.35 mL, 6.89 mmol) was added dropwise as a solution in 1 mL anhydrous dichloromethane. The resulting mixture was stirred at −78° C. for 30 minutes before being poured, while cold, into 50 mL of 5% sodium bisulfite solution. 1 N hydrochloric acid (50 mL) was added and organics were extracted with ether (3×75 mL), washed with 0.1 N hydrochloric acid, water and brine (50 mL each), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (0-10% ethyl acetate in hexanes) to give 2-bromo-5-isobutylthiophene as the major component of a mixture of two compounds. Used without further purification or characterization.

Provenance & Evidence