Ethanol → 5-Bromo-2-ethylpyridine

HRID 1387448Notes

Reaction equation

HRID 1387448 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.[CH2:10](O)[CH3:11]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:10][CH3:11])=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 693532,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 139797365-Bromo-2-ethylpyridine

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-9b409b7c85934ba19b17dad6a77c88f3
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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