Ethyl Acetate → N-[5-fluoro-1-(o-hydroxyphenyl)-1H-benzotriazole-6-yl]-1-cyclohexene-1,2-dicarboximide

Participants

Reaction Steps

A solution of N-[5-fluoro-1-(o-methoxyphenyl)-1H -benzotriazol-6-yl]-1-cyclohexene-1,2-dicarboximide (1.00 g, 0.003 mol) in methylene chloride is slowly added to a one molar boron tribromide in methylene chloride solution (5 mL, 0.005 mol) at -20° C. The reaction mixture is stirred at room temperature overnight, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a tan solid. Flash column chromatography of the solid using silica gel and 2.5% to 10% ethyl acetate in methylene chloride solutions gives the title product as a white solid, mp 274°-275° C.

Provenance & Evidence