Chloromethyl Methyl Ether → 2-Bromo-6-((methoxymethyloxy)methyl)pyridine

Under a stream of argon, (6-bromopyridine-2-yl)methanol (10 g; 53.2 mmol) was dissolved in methylene chloride (50 mL). Diisopropylethylamine (9.6 g; 74.5 mmol) and chloromethyl methyl ether (5.35 g; 66.5 mmol) were added to the reaction mixture in an ice bath, and further, the reaction mixture was stirred at room temperature for 17 hours. The reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate, and then evaporated under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (SiO2, 200 g) (toluene/ethyl acetate=10/1) to give 12.15 g (yield: 98%) of the title compound (11).

1. extractionextracted with chloroform
2. washThe organic layer was washed with water
3. dry with materialdried over sodium sulfate
4. customevaporated under reduced pressure
5. customThe resulting residue was separated
6. custompurified by silica gel column chromatography (SiO2, 200 g) (toluene/ethyl acetate=10/1)

ORD record

ord-06a7affd5aaf444bac573d4d2315c20d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187690B2