Preparation of Nitroarenes

Use care whenever performing a nitration, whether it is with a known or an unknown substance, because many compounds react vigorously under typical nitration conditions. 

Concentrated or fuming sulfuric and nitric acids are used in this procedure. These acids are very corrosive handle them with care and wear latex gloves. If the acids contact your skin, immediately flood the affected area with water, and rinse it with 5% sodium bicarbonate solution. 

Preparation Sign in at www.cengage.com/login to read the MSDSs for the chemicals used or produced in this procedure. 

Method A. Note This method yieids 1,3-dinitrobenzene from benzene or nitrobenzene and the 4-nitro derivative from chioro- or bromobenzene, benzyi chioride, or toiuene dinitro derivatives are obtained from phenoi, acetaniiide, naphthaiene, and biphenyi. 

Perform the reaction in a iarge test tube or smaii Erienmeyer fiask. Add about 0.5 g of the compound to 2 ml of concentrated suifuric acid. Add 2 ml of concentrated nitric acid dropwise to this mixture stopper the container and shake the mixture after each addition. After the addition is compiete, heat the mixture at 45 C on a water bath for about 5 min. Then pour the reaction mixture onto 15 g of ice, and coiiect the precipitate by vacuum fiitration. Recrystaiiize the soiid from aqueous ethanoi. 

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SCHEME 3.112 Preparation of nitroarenes through nitration of arylboronic acids [118]. 

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