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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence