Chloromethyl Methyl Ether → 2-Bromo-3-(methoxymethoxy)pyridine

Temperature

-20 °C

50 g of 2-bromo-3-hydroxypyridine was suspended in 200 ml of tetrahydrofuran, followed by adding 33 ml of chloromethyl methyl ether. While cooling to −20° C. and stirring, 17 g of 60% oily sodium hydride was added thereto little by little. After adding sodium hydride, the cooling medium was removed, followed by stirring at room temperature for 3.5 hours. Under cooling, ice water was added thereto little by little and the mixture was extracted with ethyl acetate. The organic phase was further washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 10-15% ethyl acetate/hexane as an eluent for separation and purification, to give 35 g of the target compound.

1. customthe cooling medium was removed
2. stirringby stirring at room temperature for 3.5 hours
3. temperatureUnder cooling
4. additionice water was added
5. extractionlittle by little and the mixture was extracted with ethyl acetate
6. washThe organic phase was further washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customthe solvent was removed
9. customfor separation and purification

ORD record

ord-e70a612ee2814bd3a210e54c81c393d2

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06599917B1