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, to which 33 ml of chloromethyl methyl ether was added. The mixture was cooled to −20° C. and 17 g of 60% oily sodium hydride was portionwise added while stirring. After the addition of sodium hydride, the refrigerant was removed and the mixture was stirred at room temperature for 3.5 hours. In an ice bath, ice water was portionwise added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (10–15% ethyl acetate/hexane), to give 35 g of the title compound.

1. additionwas added
2. customthe refrigerant was removed
3. stirringthe mixture was stirred at room temperature for 3.5 hours
4. additionIn an ice bath, ice water was portionwise added
5. extractionthe reaction mixture was extracted with ethyl acetate
6. washThe organic layer was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was removed
9. customthe residue was purified by silica gel column chromatography (10–15% ethyl acetate/hexane)

ORD record

ord-0751719e6e9444ad93d2e47b31d1d045

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112593B2