General procedure for the synthesis of 3-bromo-4,5-dimethylphenol from 1-bromo-2,3-dimethylbenzene: In a sealed tube, DPPE (0.431 g, 1.08 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.73 g, 13.5 mmol), (1,5-cyclooctadien-1-η5-indenyliridium(I) ( 0.449 g, 1.08 mmol) and 1-bromo-2,3-dimethylbenzene (1.00 g, 5.40 mmol) were dissolved in cyclohexane (6 mL) and the reaction was carried out at 100 °C for 50 hours. After completion of the reaction, the reaction mixture was concentrated and dissolved in acetone (5 mL), Oxone (3.32 g, 5.40 mmol) was added and stirred for 10 minutes. The reaction was quenched with saturated NaHSO3 solution and extracted with dichloromethane (DCM, 3 x 20 ml). The organic phases were combined, washed sequentially with saturated saline and deionized water and concentrated. The crude product was purified by silica gel column chromatography to afford 3-bromo-4,5-dimethylphenol (238 mg, 1.18 mmol, 22% yield) using dichloromethane as eluent.
