General procedure for the synthesis of 2-isopropyliodobenzene from 2-isopropylaniline: 2-isopropylaniline (27.04 g, 0.2 mol) was dissolved in 25% aqueous sulfuric acid solution (w/w, 160 mL), and diazotization reaction was carried out by slowly and dropwise addition of an aqueous solution of sodium nitrite (14 g) (26 mL) at -20 °C. The resulting diazonium salt solution was transferred to an aqueous solution (100 mL) of potassium iodide (100 g) and after 18 hours of reaction, sodium hydroxide (36 g) and water (125 mL) were added to neutralize the reaction system. The reaction mixture was extracted with hexane, the organic phases were combined and purified by silica gel column chromatography, and the target product, 2-isopropyliodobenzene, was obtained after concentration in a yield of 35.8 g, 73%. The product was identified by mass spectrometry: m/z 246 (M+). 1H NMR (CDCl3) δppm: 1.23 (d, 6H, J=6.84 Hz), 3.18 (septet, 1H, J=6.84 Hz), 6.86 (m, 1H), 7.28 (m, 2H), 7.82 (dd, 1H, J=1.24 and 7.92 Hz).
