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-f8fcf0776ef54ee9ae4d84398f2b1d2d

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790737B2