Toluene → 3-Chloro-5-methoxyphenol

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1-Chloro-3,5-dimethoxy-benzene (1.72 g, 10 mmol) in 10 mL of CH2Cl2 was cooled to −78° C., followed by 1.0 M BBr3 in toluene (10 mL, 10 mmol) added dropwise. The solution was stirred at −78° C. for 1 hour, and then allowed to warmed to room temperature over 2 hours. The reaction was quenched with water, and the aqueous layer was extracted with additional CH2Cl2. The combined organic layers were washed with brine, dried, and concentrated under pressure. The residue was purified by silica gel column chromatography eluting with 1:1 EtOAc/Hexanes to give 0.51 g of the title compound. MS (APCI) m/e 159 (M+H)+, 1H NMR (500 MHz, DMSO-d6): □ 9.88 (s, 1H), 6.43 (m, 1H), 6.39 (m, 1H), 6.28 (m, 1H), 3.70 (s, 3H).

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