Hydrochloric Acid → 4-Benzyloxy-2-iodo-5-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-benzyloxy-2-iodo-5-methoxybenzamide (reference example 6-3) (5.25 g) and dichloromethane (70 mL) were added triethylamine (8.2 mL) and trifluoromethanesulfonic anhydride (4.6 mL) at 0° C. The mixture was stirred at 0° C. for 20 minutes, at room temperature for 3.5 hours and at reflux temperature for an hour. After cooling to 0° C., to the mixture were added triethylamine (4 mL) and trifluoromethanesulfonic anhydride (2.3 mL). After stirring at room temperature overnight, to the mixture were added ice-water and 1 mol/L hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. A mixture of the residue, ethyl acetate, dichloromethane, silicagel and aminopropylsilicagel was stirred for 30 minutes. The mixture was passed through a layer of Celite (registered mark). The filtrate was concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (3.72 g).

Provenance & Evidence