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

HRID 1626927Notes

Reaction equation

HRID 1626927 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-fc4538412e4b40b1a6775ea2aefc4e4f
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

Loading…