Nitric Acid → 5-Methyl-2-nitro-3-phenylbenzofuran

Participants

Reaction Steps

To a solution of 25 g (0.0875 mole) of 2-bromo-5-methyl-3-phenylbenzofuran and 16.5 g of cyclohexene-4-carboxylic acid in 150 ml of acetic acid is added 17.5 g of sodium nitrite, then 17.5 ml of nitric acid is added dropwise with stirring. The mixture is stirred at about 25° C. for about three hours, then poured onto ice. The mixture is then extracted with diethyl ether. The ether solution is washed with 10% sodium bicarbonate solution, saturated sodium carbonate solution and dried. The dried solution is evaporated under vacuum to provide a yellow residue. The residue is recrystallized from carbon tetrachloride, then cyclohexane to provide yellow crystals of 5-methyl-2-nitro-3-phenylbenzofuran, m.p. 144.5°-146° C.

Provenance & Evidence