4-Fluorophenol → 2-(4-Fluorophenoxy)thiophene

Participants

Reaction Steps

A solution of 4-fluorophenol (22.42 g, 200 mmol), 2-bromothiophene (65.22 g, 400 mmol), potassium carbonate (42.84 g, 310 mmol), and copper powder (6.35 g, 100 mmol) in pyridine (200 mL) was refluxed for 18 hours. It was then cooled to ambient temperature and filtered through Celite. The filtrate was diluted with ethyl acetate (500 mL) and washed with water (3×300 mL). The organic phase was dried over MgSO4 and concentrated. The resulting residue was chromatographed (silica gel; hexanes) to afford 3.67 g (9%) of 2-(4-fluorophenoxy)thiophene as a colorless oil.

Provenance & Evidence