2-(2-bromo-5-methoxyphenyl)ethanol

5020-41-7

75534-35-9

General procedure for the synthesis of 2-(2-bromo-5-methoxyphenyl)ethanol from 2-(3-methoxyphenyl)ethanol: (i) 3-methoxyphenylethanol (1.18 g, 7.8 mmol) and pyridine (0.75 mL, 9.3 mmol) were dissolved in anhydrous dichloromethane (10 mL) under nitrogen protection, stirred and cooled to 0 °C. Subsequently, bromine (0.47 mL, 18.0 mmol) was added slowly and dropwise. The reaction mixture was continued to be stirred at room temperature for 4 h. The solution was orange in color. Upon completion of the reaction, the reaction was quenched by the addition of 10% aqueous sodium bisulfite and extracted with dichloromethane. The organic phases were combined, washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography with gradient elution using hexane and ethyl acetate (10:1, 8:1, 5:1) as eluents to afford the target compound 2-(2-bromo-5-methoxyphenyl)ethanol as a colorless oil (1.5 g, 83.2% yield).1H-NMR (CDCl3) data: δ 7.43 (d, J = 8.8 Hz, 1H) , 6.83 (d, J = 3.3 Hz, 1H), 6.67 (dd, J = 8.8, 3.3 Hz, 1H), 3.91-3.81 (m, 2H), 3.78 (s, 3H), 2.99 (t, J = 6.6 Hz, 2H).