Methyl iodide → 3-Fluoro-2-methoxybenzaldehyde

Participants

Reaction Steps

A mixture of 3-fluorosalicylaldehyde (3.52 g, 25.12 mmol) and cesium carbonate (20.46 g, 62.81 mmol) in N,N-dimethylformamide (30 mL) is treated with iodomethane (3.13 mL, 50.2 mmol) and stirred at room temperature under nitrogen for 2 h. The reaction mixture is diluted with diethyl ether (150 mL) and washed with 0.5 M hydrochloric acid (2×150 mL). The organic portion is dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3.42 g (88%) of the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.59 (d, 1H), 7.32 (dd, 1H), 7.04 (m, 1H), 4.04 (s, 3H).

Provenance & Evidence