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Step 2: Synthesis of 3-bromo-6-methoxy-2,4-dimethylpyridine
In a 500 mL three-necked round-bottomed flask, nitrogen displacement was performed and an inert atmosphere was maintained. To the flask was added 5-bromo-4,6-dimethylpyridin-2(1H)-one (3.90 g, 19.30 mmol, 1.00 eq.), dichloromethane (150 mL) and silver carbonate (Ag2CO3, 7.34 g, 0.0266 mol, 1.40 eq.). Iodomethane (Mel, 28.4 g, 0.2 mol, 10.50 eq.) was slowly added to the mixture with stirring. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solid was collected by filtration and the filter cake was washed with dichloromethane (50 mL). The combined filtrates were concentrated under reduced pressure to give 3.91 g (94% yield) of 3-bromo-6-methoxy-2,4-dimethylpyridine as a brown oil. Mass Spectrometry (ESI) m/z measured value: C8H10BrNO [M + H]+: 216. | [References]
[1] Patent: US2015/315198, 2015, A1. Location in patent: Paragraph 0393; 0394 [2] Journal of Organic Chemistry, 2004, vol. 69, # 26, p. 9215 - 9223 |
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