Sodium Carbonate → 2-(4-Fluorophenyl)thiophene

Participants

Reaction Steps

A solution of 2-bromothiophene (233.0 g, 1.43 mol), 4-fluorophenyl boronic acid (200.0 g, 1.43 mol), bis(triphenylphosphine)palladium(II) dichloride (10.0 g, 14.2 mmol) and aqueous Na2CO3 (454.5 g, 4.3 mol in 1.5 L of H2O) in 1,2-dimethoxyethane (2 L) was stirred at 75-80° C. (internal temperature) for 2 hours. The resulting mixture was cooled to room temperature and then stirred overnight. The solid was separated and discarded. The liquid was washed with water (2×500 mL). The combined aqueous layer was extracted with diethylether (2×500 mL). The combined organic layers were then dried over NaCl, concentrated and purified by flask distillation to yield the title compound as a white solid.

Provenance & Evidence