General procedure for the synthesis of 3-bromo-4-methoxyphenol from 3-bromo-4-methoxyphenyl acetate: a solution of potassium hydroxide (290 mg, 5.19 mmol) in water (2.5 mL) was added to a solution of 3-bromo-4-methoxyphenyl acetate (1.2 g, 4.9 mmol) in methanol (18.5 mL). The reaction mixture was stirred at room temperature for 30 min, followed by removal of the solvent under reduced pressure. Water (40 mL) was added to the residue and 1.2 M aqueous hydrochloric acid (4.3 mL) was added dropwise until the mixture was acidic. The mixture was extracted with dichloromethane (2 x 40 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated under reduced pressure to give 3-bromo-4-methoxyphenol (976 mg, 98% yield) as a light yellow solid.LCMS analysis (Method A): retention time (RT) = 2.11 min; no ionization was observed.TLC analysis: Rf = 0.28 (unfolding reagent ratio 1:4 ethyl acetate:hexane).
