Nitric Acid → 4,5-Dichloro-2-nitrophenol

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A 250 mL roundbottom flask charged with 3,4-dichlorophenol (3.053 g, 18.7 mmol) in 50 mL CH2Cl2 was cooled to 0° C. in an ice bath. To the stirred solution was added concentrated H2SO4 (1.56 mL, 28.1 mmol). The solution became turbid. To this mixture was added concentrated HNO3 (1.2 mL, 18.7 mmol), dropwise and carefully to maintain a temperature below 5° C. The reaction was stirred for 30 min at 0° C., then cooled with an ice bath and quenched with 150 mL H2O. The layers were separated and the aqueous layer was extracted once with 35 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, concentrated under vacuum and purified using flash chromatography (10% EtOAc/hexanes as eluent) to yield the desired nitrophenol as a bright yellow solid (1.793 g).

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