Methyl iodide → 2-Bromo-3-methoxypyridine

Temperature

90 °C

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).

1. distillationto distill off methanol
2. temperatureAfter the reaction solution was cooled down to 10° C.
3. customAfter the completion of the reaction
4. extractionextracted twice with chloroform
5. washThe combined chloroform layer was washed with a 1 mol/L sodium hydroxide solution
6. washwashed twice with a saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. distillationThen, the solvent was distilled off under reduced pressure

ORD record

ord-251122566eb94ae5ad78da5fb790734b

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08277777B2