Dichloromethane → N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4, 5-dihydroxyphenyl) propenamide

Participants

Reaction Steps

Demethylation was effected in the same manner as in Example 2 with N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4-hydroxy-5-methoxyphenyl) propenamide (1.38 g, 3.39 mmol) and 1M solution of boron tribromide in methylene chloride (8.5 ml, 8.5 mmol). The resultant solid was mixed with ethanol, refluxed for 10 minutes, allowed to cool to room temperature and filtered to give the objective N-(3-chlorophenyl)-2-cyano-3-(3-bromo-4, 5-dihydroxyphenyl) propenamide (360 mg, 27% in yield).

Provenance & Evidence