Methyl iodide → 3-Fluoro-4-nitroanisole

Participants

Reaction Steps

A mixture of 3-fluoro-4-nitrophenol (5.0 g, 31.8 mmol), iodomethane (13.5 g, 95.4 mmol), and potassium carbonate (16.7 g, 159 mmol) in acetone (80 mL) was heated to reflux for 16 hours. The mixture was cooled and evaporated under vacuum, and the partitioned between water (75 mL) and methylene chloride (75 mL) and the aqueous phase was extracted with methylene chloride (2×75 mL). The combined organic phases were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 5.30 g, in 97% yield: 1H NMR (CDCl3) δ 3.90 (s, 3H), 6.70-6.79 (m, 2H), 8.09 (t, J=9.1 Hz, 1H).

Provenance & Evidence