Iodoethane → 3-Bromo-1-ethyl-2(1H)-pyridinone

HRID 539124Notes

Reaction equation

HRID 539124 reaction equation
[Br:1][C:2]1[C:3]([OH:8])=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:15](I)[CH3:16]>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 178517701HCID 178517701, compound

Product 1

HCID 122105393-Bromo-1-ethyl-2(1H)-pyridinoneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-bromopyridin-2-ol (1.0 g, 5.75 mmol) in DMF (6 mL) was treated with cesium carbonate (1.87 g, 5.75 mmol) and ethyl iodide (1.38 mL, 17.2 mmol). The mixture was heated at 80° C. for 4 hours. The solvent was concentrated and the residue taken in EtOAc, washed with brine, dried (phase separator silicone treated filter paper), concentrated and purified on silica gel (1:2 hexane/ether) to provide 3-bromo-1-ethylpyridin-2(1H)-one (0.905 g, 78% yield) as a yellow oil.

Workup

  1. concentrationThe solvent was concentrated
  2. washwashed with brine
  3. customdried
  4. addition(phase separator silicone treated filter paper)
  5. concentrationconcentrated
  6. custompurified on silica gel (1:2 hexane/ether)

Sources & evidence

ORD record
ord-6530cf86fe2b4a1f8d0ad66752c60f8d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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