2-bromoaniline (5 g, 29 mmol) dissolved in CH3CN (80 mL) was added to HCl (15 mL conc, 50 mL water) and then, the mixture was cooled to 0 °C. It was added a solution of NaNO2 (2.4 g, 34.87 mmol) in water (50 mL). After that, the reaction was kept at lower than 5 °C for 30 min and it was added a solution of potassium iodide (7.23 g, 43.59 mmol) in water (50 mL). After addition, the reaction was kept at room temperature overnight, poured into water (300 mL), and extracted with CH2Cl2. The organic phase was dried over MgSO4. Finally, 2-Bromo-4-tert-butyl-1-iodo-benzene was obtained after purification.
