Ethanol → 5-Bromo-2-ethoxypyridine

HRID 1108399Notes

Reaction equation

HRID 1108399 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.[CH2:10]([OH:12])[CH3:11]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([O:12][CH2:10][CH3:11])=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 693532,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 8172375-Bromo-2-ethoxypyridine

Procedure

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.

Workup

  1. dissolutionuntil completely dissolved
  2. stirringthe resulting mixture was stirred
  3. temperatureat reflux for 16 hr
  4. customThe solvent was removed in vacuo
  5. customthe residue partitioned between water and EtOAc
  6. extractionAfter extraction with EtOAc (2×)
  7. washthe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-42e3e2aef2e340d58847d72349c42d9b
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

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