Reaktion #2146703

Reaktionsgleichung

2-bromo-3-hydroxypyridine

sodium methoxide

methyl iodide

→

2-bromo-3-methoxypyridine

Lösungsmittel

dimethylsulfoxide

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle