4-Bromo-2,6-dimethylphenol

576-26-1

2374-05-2

In a 10 mL two-neck flask equipped with a reflux condenser, 2,6-dimethylphenol (0.25 mmol) and tetrabutylammonium bromide (161.2 mg, 0.50 mmol) were added. The flask was evacuated and backfilled three times with argon. To the reaction mixture was added ultrapure water (0.5 mL), trifluoroacetic acid (57.5 μL, 0.75 mmol) and 30% hydrogen peroxide (77 μL, 0.75 mmol). The reaction mixture was stirred at 25 °C under argon protection. Upon completion of the reaction, the reaction was quenched with 1:1 saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate and extracted with ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. 1,3,5-Trimethoxybenzene or hexamethylbenzene was added as an internal standard and the NMR yield of the product was determined by 1H NMR analysis. The spectral data obtained for 4-bromo-2,6-dimethylphenol were consistent with those of commercially available standards.