3282-56-2

35779-04-5

3282-56-2

GENERAL STEPS: Add 1-tert-butyl-4-iodobenzene (0.5 mmol), copper(II) trifluoromethanesulfonate (45 mg, 0.125 mmol), potassium nitrite (KNO2, 128 mg, 1.5 mmol), and anhydrous dimethylsulfoxide (DMSO, 0.6 mL) to an oven-dried pressure tube under nitrogen atmosphere. The pressure tube was sealed with a polytetrafluoroethylene screw cap with a microvalve and purged through nitrogen for 5 min to displace the air. The mixture was stirred at room temperature for 10 minutes and then gradually warmed to 130 °C and the reaction was maintained at this temperature for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature, washed with excess ice water and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (Table 2, entries 1-18) or basic alumina column chromatography (Table 2, entries 19-23) using a mixture of ethyl acetate and hexanes as eluent to give 1-tert-butyl-4-nitrobenzene in good final yield.