Iodoethane → 5-Bromo-1-ethylpyridin-2(1H)-one

HRID 518258Notes

Reaction equation

HRID 518258 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[N:8][CH:9]=1.I[CH2:12][CH3:13]>C1COCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7](=[O:10])[N:8]([CH2:12][CH3:13])[CH:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178515818HCID 178515818, compound

Product 1

HCID 122105365-Bromo-1-ethylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 1.34 g, 0.056 mol) in THF (10 mL), a solution of 5-bromopyridin-2-ol (2.5 g, 0.014 mol) in THF (50 mL) was added and the resulting mixture was stirred at RT for 1 h. To this mixture, iodoethane (10.9 g, 0.07 mol) was added and the mixture was stirred at RT overnight. The mixture was quenched with water and washed with NH4Cl solution. The organic phase was separated, then concentrated in vacuo and the residue was purified by flash chromatography on silica gel (50-100% PE-AE) to afford 5-bromo-1-ethylpyridin-2(1H)-one.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe mixture was quenched with water
  3. washwashed with NH4Cl solution
  4. customThe organic phase was separated
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (50-100% PE-AE)

Sources & evidence

ORD record
ord-7a5fee37936943a785b9e27f46275b64
Source dataset
uspto-grants-2015_08
Patent number
US09115141B2

Reaction notes

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