Water → 2-(4-Iodophenoxy)pyrimidine

Participants

Reaction Steps

A mixture of 2-phenoxypyrimidine (int AY) (4.03 g, 0.0234 mol) and N-iodosuccinimide (10.52 g, 0.0468 mol) in trifluoroacetic acid (40 mL) and trifluoroacetic anhydride (8 mL) was heated at reflux for 4 hours. The mixture was allowed to cool to ambient temperature and water (75 mL) was added. The mixture was extracted with three times with 50 mL. The combined organic layers were washed twice with saturated aqueous sodium bicarbonate (50 mL), twice with 10% aqueous sodium thiosulfate (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate, filtered and the solvent was removed in vacuo. The crude solid was purified by flash column chromatography on silica gel using n-heptane/ethyl acetate (3:1) as an eluent to give 2-(4-iodophenoxy)pyrimidine as a light yellow solid (3.49 g, 0.0117 mol): 1H NMR (CDCl3, 400 MHz) 8.57 (d, 2H), 7.73 (d, 2H), 7.07 (t, 1H), 6.98 (d 2H); TLC (n-heptane/ethyl acetate=1:1) Rf 0.45.

Provenance & Evidence