Methyl iodide → Methyl 3-methoxy-5-nitrobenzoate

Participants

Reaction Steps

A mixture of methyl iodide (0.200 mL, 3.2 mmol), 93A (328 mg, 1.66 mmol), and potassium carbonate (250 mg, 1.80 mmol) in DMF (2 mL) was stirred overnight at rt. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined organic layers were washed with water and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient of 0 to 50% ethyl acetate in hexanes) to give 93B (0.22 g, 63%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.95 (s, 3H) 3.98 (s, 3H) 7.87-7.90 (m, 1H) 7.90-7.93 (m, 1H) 8.44-8.48 (m, 1H); LC/MS 212 (M+H).

Provenance & Evidence