Iodoethane → 2-Bromo-3-ethoxypyridine

HRID 361811Notes

Reaction equation

HRID 361811 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9](I)[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 106319262-Bromo-3-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromopyridin-3-ol (3.00 g), ethyl iodide (3.44 ml), anhydrous potassium carbonate (4.28 g) and dry dimethylformamide (34 ml) is stirred under nitrogen at 80°-85° for 2.5 hrs, concentrated to remove solvent, diluted with ethyl acetate (75 ml) and water (40 ml), and the layers are separated. The aqueous phase is extracted with ethyl acetate (75 ml) and the combined organic phase is washed with saline (30 ml), dried over sodium sulfate, and concentrated under reduced pressure to give the title compound, NMR (CDCl3) 7.97, 7.20, 7.12, 4.11 and 1.50δ.

Workup

  1. concentrationconcentrated
  2. customto remove solvent
  3. additiondiluted with ethyl acetate (75 ml) and water (40 ml)
  4. customthe layers are separated
  5. extractionThe aqueous phase is extracted with ethyl acetate (75 ml)
  6. washthe combined organic phase is washed with saline (30 ml)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd415e3c8d5c454da0f7a89c47457c77
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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