Nitric Acid → 3-Bromo-4-(2'-methylbutyl)benzoic acid

Participants

Reaction Steps

A solution of silver nitrate (177 g, 1.1 mol) in water (500 ml) was dropwise added to a solution in water (500 ml), of a mixture of (S)-4-(2'-methylbutyl)benzoic acid (200 g, 1.0 mol), nitric acid (680 ml) and bromine (183 g, 1.1 mol), under ice-cooling, followed by agitating the mixture at room temperature for 5 hours, feeding it into ice water, filtering deposited crystals, adding a 10% sodium carbonate aqueous solution (2 l), sufficiently agitating the mixture, filtering off a remaining insoluble substance, acidifying the filtrate with sulfuric acid, filtering deposited crystals and recrystallizing from acetic acid (1 l) to obtain 3-bromo-4-(2'-methylbutyl)benzoic acid (106.0 g, m.p. 78.8°-79.7° C.).

Provenance & Evidence