Toluene → 2'-Sulfamoyl-biphenyl-4-carboxylic acid

Participants

Reaction Steps

2-Bromobenzenesulfonamide (800 mg) and 4-carboxyphenyl boronic acid (563 mg) were suspended in a solvent mixture of toluene (5 mL) and water (5 mL). To the reaction mixture, tetrakis(triphenylphosphine)palladium (392 mg) and sodium carbonate anhydrate (1.08 g) were sequentially added, and the resultant mixture was heated under reflux overnight. The resultant mixture was cooled to room temperature, and diethyl ether and water were added thereto for partitioning the mixture. The organic layer was extracted twice with water. All the resultant aqueous layers were combined together, and 12N aqueous hydrochloric acid was added thereto to acidfy. The mixture was concentrated to about 20 mL under reduced pressure, and the precipitated colorless powder was recovered by filtration, followed by drying under reduced pressure, to thereby give the title compound (539 mg).

Provenance & Evidence