Methanol → 3-Bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine

A solution of (3-bromo-6-methoxypyridin-2-yl)methanol (10.6 g, 48.6 mmol) synthesized by the method described in Organic & Biomolecular Chemistry 1 (16) 2865-2876 (2003) in dichloromethane (150 mL) was successively added dropwise with N,N-diisopropylethylamine (31.4 g, 243 mmol) and chloromethyl methyl ether (13.3 g, 165 mmol) under ice cooling. The mixture was warmed to room temperature, stirred for 16 hours, and then added with methanol (30 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1) to obtain 3-bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine (12.1 g, 95%) as pale yellow oil.

1. stirringthe mixture was stirred for 30 minutes
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1)

ORD record

ord-8e606dfde6d14a19ae3700652b672f5f

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012989B2