[Synthesis]
General procedure for the synthesis of 5-bromo-2-iodoisopropylbenzene from 2-isopropyliodobenzene: 1-iodo-2-isopropylbenzene (1.5 g, 6.1 mmol) was mixed with silver sulfate (1.0 g, 3.1 mmol), concentrated sulfuric acid (5.5 mL), water (0.6 mL) and bromine (0.3 mL, 6.4 mmol) to form a three-phase suspension. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the mixture was poured into a mixture of ether (150 mL) and water (75 mL). The solids were removed by filtration and the organic and aqueous layers were separated. The organic layer was concentrated under vacuum and the residue was purified by preparative high performance liquid chromatography (HPLC) to afford the target product 5-bromo-2-iodoisopropylbenzene as a white solid (189 mg, 10% yield). [0257] 1H NMR (500 MHz, DMSO-d6) δ 1.18 (d, J = 6.8 Hz, 6H), 3.07 (qn, J = 6.8 Hz, 1H), 7.15 (dd, J = 8.4,2.5 Hz, 1H), 7.46 (d, J = 2.4 Hz, 1H), 7.75 (d, J = 8.4 Hz, 1H). 2D NOE (500 MHz, DMSO-d6): cross peak between δ 1.18 and 7.46. |