Iodoethane → 1-Ethoxy-2-iodo-4-nitrobenzene

Participants

Reaction Steps

A suspension of 2-iodo-4-nitrophenol (21 g, 79.2 mmol) [ref: Kometani, T.; Watt, D. S.; Ji, T., Tetrahedron Lett. (1985), 26(17), 2043], ethyl iodide (9 mL, 0.48 mol) and potassium carbonate (40.7 g, 0.3 mol) in 100 mL of N,N-dimethylformamide was heated at 70° C. for 3 hours. The reaction was cooled to room temperature and ethyl acetate was added. The inorganic salts were filtered and washed with ethyl acetate. The organic material was washed with water (3×) and brine, dried over magnesium sulfate and filtered. Upon concentration of the filtrate a solid appeared. This solid was filtered and washed with hexanes to give 5.2 g of 1-ethoxy-2-iodo-4-nitrobenzene as white crystals. Concentration of the filtrate provided an additional 11.3 g of the desired product, mp 81-83° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.42 (t, 3H), 4.26 (q, 2H), 7.18 (d, 1H), 8.26 (dd, 1H), 8.55 (d, 1H)

Provenance & Evidence