Ethanol → HCID 10402349, compound

Participants

Reaction Steps

A solution of 2,5-dibromothiophene (1.0 g, 4.1 mmol), 4-methylcarboxyphenylboronic acid (370 mg, 2.05 mmol), Pd(PPh3)4 (30 mg) and K2CO3 (1.13 g, 8.2 mmol) in toluene (20 mL) containing 5 mL EtOH and 1 mL water were refluxed overnight under argon. After cooling to room temperature, the solvent was evaporated and residue partitioned between EtOAc and water. Organic layer was separated, dried, evaporated and residue purified by combiflash to afford 4-(5-Bromo-thiophen-2-yl)-benzoic acid methyl ester (200 mg) which was redissolved in toluene (10 mL), containing 4-hexyloxyphenylboronic acid (222 mg, 0.1 mmol), Pd(PPh3)4 (30 mg) and K2CO3 (189 mg, 0.13 mmol) containing 3 mL EtOH and 0.5 mL water and refluxed overnight. The resulting solution was cooled and the solid formed filtered, washed with water and methanol and dried (130 mg). It was subjected to hydrolysis using dioxane-water/NaOH overnight to afford 4-[5-(4-Hexyloxy-phenyl)-thiophen-2-yl]-benzoic acid

Provenance & Evidence