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ChemicalBook CAS DataBase List 2-Bromo-3-hydroxy-6-methylpyridine
23003-35-2

2-Bromo-3-hydroxy-6-methylpyridine synthesis

2synthesis methods
3-Hydroxy-6-methylpyridine

1121-78-4

2-Bromo-3-hydroxy-6-methylpyridine

23003-35-2

1. Synthesis of 2-bromo-3-hydroxy-6-methylpyridine. To a 125 mL pyridine solution of 5-hydroxy-2-methylpyridine (8.80 g, 80.6 mmol) was slowly added dropwise 50 mL pyridine solution of bromine (14.18 g, 88.7 mmol). After the dropwise addition was completed, the temperature of the reaction mixture was raised to 40 °C. After 1 hour of reaction, the pyridine solvent was evaporated under reduced pressure. The resulting solid was suspended in 200 mL of water and stirred overnight. The solid product was collected by filtration and dried to give the target compound 2-bromo-3-hydroxy-6-methylpyridine as a brown solid (8.05 g, 53.1% yield). The product was characterized by 1H NMR (500 MHz, CDCl3): δ 2.21 (s, 3H), 6.73 (d, J = 8.1 Hz, 1H), 6.94 (d, J = 8.1 Hz, 1H), 9.36 (br s, 1H).

-

Yield:23003-35-2 74%

Reaction Conditions:

with bromine in pyridine;Ambient temperature;

References:

Ross Kelly;Lang, Fengrui [Tetrahedron Letters,1995,vol. 36,# 30,p. 5319 - 5322]

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