Sodium Carbonate → 2-(4-Fluorophenyl)thiophene

Participants

Reaction Steps

A solution of sodium carbonate (1.63 g) in H2O (7.65 ml), 4-fluorobenzeneboronic acid (1.03 g) and tetrakis(triphenylphosphine) palladium(0) (70.9 mg) were added successively to a solution of 2-bromothiophene (1.00 g) in dimethoxyethane (12.3 ml). The mixture was refluxed for 4 hours. The mixture was cooled to ambient temperature and partitioned between AcOEt and H2O. The organic layer was washed with 0.5N aqueous NaOH solution and saturated aqueous NaCl solution, dried over MgSO4 and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: n-hexane and then AcOEt in n-hexane 10%). The solvent was evaporated in vacuo to give 1.05 g of 2-(4-fluorophenyl)thiophene as a white solid.

Provenance & Evidence