A solution consisting of toluene (100 mL), ethanol (50 mL), and water (50 mL) was sparged with dry nitrogen for 45 minutes. To the mixture was added methyl 4-bromo-3-methoxybenzoate of step B (26.5 mmol), o-tolylboronic acid (29.1 mmol), and sodium carbonate (112.5 mmol). The mixture was sparged with nitrogen for an additional ten minutes. Terakis(triphenylphosphine)palladium(0) (1 mmol) was added to the mixture, which was then heated at 105° C. for 6 hours. The mixture was cooled and the organic phase was washed three times in sequence with saturated aqueous sodium carbonate and brine. The organics were dried over anhydrous sodium sulfate, filtered, and evaporated to an oil. Flash chromatography of the residue on silica gel using dichloromethane/hexane (3:1) yielded the title compound as a clear oil (6.7 g, 99%).
