Ethanol → 5-Bromo-2-ethoxypyridine

Participants

Reaction Steps

Sodium metal (4.87 g, 0.212 mol) was added to ethanol (200 mL) and stirred until completely dissolved. To this solution was added 2,5-dibromopyridine 9-1 (10 g, 0.0424 mol) and the resulting mixture was stirred at reflux for 16 hr. The solvent was removed in vacuo and the residue partitioned between water and EtOAc. After extraction with EtOAc (2×), the organic layer was washed with brine, dried (MgSO4) and concentrated to give 9-2 as a red-brown solid which was used as such in the next step.

Provenance & Evidence