Methyl iodide → 5-Methoxy-2-nitrobenzaldehyde

Participants

Reaction Steps

To a solution of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol) in 3.6 mL of dry N,N-dimethylformamide was added sodium hydride (94 mg, 55%, 2.1 mmol) under nitrogen at 0° C. After the solution was stirred at room temperature for 30 min, methyl iodide (0.17 mL, 2.7 mmol) was added with additional stirring for 30 min. The reaction mixture was quenched with saturated NH4Cl aqueous solution at 0° C., and the mixture was extracted with diethyl ether. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20 to 70/30) to obtain the title compound as a pale yellow powder (298 mg, 91%).

Provenance & Evidence