Water → HCID 21330915, compound

Participants

Reaction Steps

To a solution of 12.4 g (0.041 mole) of 2-bromo-3-(3',4'-dimethylphenyl)benzofuran in 400 ml of acetic acid is added 7.8 g (0.062 mole) of cyclohexene-4-carboxylic acid and a solution of 5 g (0.062 mole) of dinitrogen tetroxide in 25 ml of acetic acid. After stirring for about 16 hours the mixture is poured into cold water to give a gummy solid. The solid is collected, washed with water and dissolved in diethyl ether. The ether solution is washed with water, 10% sodium bicarbonate solution and saturated sodium chloride solution, then dried. Evaporation provides a residue which is dissolved in carbon tetrachloride and chromatographed on silica gel, eluting with carbon tetrachloride and combining the fractions consisting of chiefly one component according to thin layer chromatography. The solid is recrystallized from aqueous ethanol, then from isopropanol to provide yellow solid 3-(3',4'-dimethylphenyl)-2-nitrobenzofuran, m.p. 125°-133° C. which is about 90% pure, containing about 10% of monobromo-3-(3',4'-dimethylphenyl)-2-nitrobenzofuran.

Provenance & Evidence