Hydrochloric Acid → 4-(4-(Isopropylthio)phenyl)thiophene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of commercially available 4-(isopropylthio)phenylboronic acid (735 mg, 3.75 mmol), 4-bromothiophene-2-carboxylic acid (776 mg, 3.75 mmol), Bis(triphenylphosphine)palladium (II) chloride (131 mg, 0.188 mmol), acetonitrile (7.5 mL) and aqueous sodium carbonate (1M, 7.5 mL) was heated to 150° C. by microwave irradiation (Biotage Intiator™ Sixty, 0-300 W, pre-stirring 2 minutes) for 5 minutes under an argon atmosphere. The reaction mixture was cooled to ambient temperature, diluted with water (75 mL), and extracted with EtOAc (2×50 mL). The aqueous layer obtained was then acidified with aqueous HCl (3.0M) to pH 2 and extracted with EtOAc (2×50 mL). The combined organic layers were dried over sodium sulfate, filtrated and concentrated to afford compound 73 (990 mg) which was used in next step without further purification.

Provenance & Evidence