4-Bromo-2-nitrophenol → 2-Amino-4-Bromophenol

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To a stirred solution of 4-bromo-2-nitrophenol (5.00 g, 22.9 mmol) in MeOH (120 mL) was added tin(II) chloride dihydrate (15.53 g, 68.8 mmol). The reaction mixture was heated at reflux and monitored by LC/MS. When significant reduction was complete, the reaction mixture was cooled to rt, poured over ice, and made basic (pH 9) with 50% saturated NaHCO3. The aqueous layer was extracted with EtOAc (2×150 mL) and the combined extracts washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 2-amino-4-bromophenol as a dark gray solid. 1H NMR (CDCl3, 300 MHz) δ 9.29 (br s, 1H), 6.71 (d, 1H), 6.56 (d, 1H), 6.49 (dd, 1H), 4.83 (br s, 2H).

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