Chloromethyl Methyl Ether → 2-Bromo-5-(methoxymethoxy)pyridine

To a solution of 6-bromopyridin-3-ol (25 g, 144 mmol) in DMF (300 mL) at 0° C. under N2 is added portionwise NaH (5.7 g, 144 mmol) over 5 min. The reaction was stirred 1 h, then chloro(methoxy)methane (12 g, 144 mmol) was added and the reaction stirred an additional 1 h at 0° C. Saturated sodium bicarbonate (500 mL) was added slowly and the suspension stirred 30 min and warmed to rt. The solution was extracted with EtOAc (3×400 mL), the combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as a brown oil.

1. stirringthe reaction stirred an additional 1 h at 0° C
2. stirringthe suspension stirred 30 min
3. extractionThe solution was extracted with EtOAc (3×400 mL)
4. washthe combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated in vacuo

ORD record

ord-8139b49a9c4945e694dea03a4c0b2ea9

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745484B2