Реакция #2146703

Уравнение реакции

2-bromo-3-hydroxypyridine

sodium methoxide

methyl iodide

→

2-bromo-3-methoxypyridine

Растворители

dimethylsulfoxide

methanol

Условия реакции

Обработка

1. 1
   workup.DISTILLATIONto distill off methanol
2. 2
   ТемператураAfter the reaction solution was cooled down to 10° C.
3. 3
   ДругоеAfter the completion of the reaction
4. 4
   Экстракцияextracted twice with chloroform
5. 5
   ПромывкаThe combined chloroform layer was washed with a 1 mol/L sodium hydroxide solution
6. 6
   Промывкаwashed twice with a saturated sodium chloride solution
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure

Методика

100.0 g (corresponding to 0.575 mol) of 2-bromo-3-hydroxypyridine was dissolved in 310 mL of dimethylsulfoxide, and 575 mL (corresponding to 0.575 mol) of a solution of 1 mol/L sodium methoxide in methanol was added thereto. Then, the reaction solution was heated to 90° C. to distill off methanol. After the reaction solution was cooled down to 10° C. or lower, 93.9 g (corresponding to 0.662 mol) of methyl iodide was added thereto, and the mixture was stirred at room temperature for 20.5 hours. After the completion of the reaction, the reaction solution was poured into ice water and extracted twice with chloroform. The combined chloroform layer was washed with a 1 mol/L sodium hydroxide solution, washed twice with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure, to obtain 65.4 g (corresponding to 0.348 mol) of 2-bromo-3-methoxypyridine (FIG. 1, Step 1).

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