Methanol → 5-Bromo-2-methoxypyridine

Sodium hydride (2.0 g of a 60% dispersion in mineral oil) was added portionwise to methanol (30 ml) with stirring and cooling with an ice-bath. 2,5-Dibromopyridine (2.37 g) was added to the mixture and the mixture stirred at reflux for 16 hours. The methanol was removed by evaporation. Water (15 ml) was added to the residue and the mixture was extracted with dichloromethane (3×15 ml). The organic extracts were combined, dried (MgSO4) and evaporated to give 5-bromo-2-methoxypyridine (2.0 g) as an oil, NMR: 3.85(3H,s), 6.83(1H,d), 7.9(1H,dd) and 8.3(1H,d).

1. temperaturecooling with an ice-bath
2. stirringthe mixture stirred
3. temperatureat reflux for 16 hours
4. customThe methanol was removed by evaporation
5. additionWater (15 ml) was added to the residue
6. extractionthe mixture was extracted with dichloromethane (3×15 ml)
7. dry with materialdried (MgSO4)
8. customevaporated

ORD record

ord-6e2a181c12d049eebb5288711dabbc3a

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05714496