Phosphorus oxybromide → 2-Bromo-4-methyl-5-nitropyridine

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To a suspension of 2-hydroxy-4-methyl-5-nitropyridine (1 g, 6.5 mmol) in dichloroethane (10 mL) was added a solution of phosphorus oxybromide (2.8 g, 9.7 mmol) in dichloroethane (10 mL). The reaction mixture was heated under reflux for 4 h, then cooled to rt and quenched with water (40 mL). The layers were separated and the aqueous layer extracted into dichloromethane (2×3 mL). The combined organics were dried (MgSO4), concentrated in vacuo and chromatographed on silica gel eluting with dichloromethane to give the title compound as a pale yellow solid. δH (CDCl3): 2.63 (3H, s), 7.52 (1H, s), 8.96 (1H, s).

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