Potassium Carbonate → 5-(4-Fluorophenyl)-3-thiophenecarboxylic acid ethyl ester

Participants

Reaction Steps

A mixture of 5-bromo-thiophene-3-carboxylic acid ethyl ester (1.0 g, 4.5 mmol), 4-fluorophenylboronic acid (0.88 g. 6.4 mmol), potassium carbonate (1.75 g, 12 mmol) and tetrakistriphenylphosphinepalladium(0) (0.2 g, 4 mole %) in a 50:50 mixture of DME/H2O (10 mL) was heated at reflux temperature overnight under a nitrogen atmosphere. The resulting reaction mixture was cooled, diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over sodium sulfate and rotary evaporated. The residue was purified by flash chromatography (silica gel; 2% acetone/hexane) to obtain 5-(4-fluorophenyl)-3-thiophenecarboxylic acid ethyl ester as an oil (1.0 g, 88%). MS: m/z=251 (M+1).

Provenance & Evidence