Water → 1-(5-Bromopyridin-3-yl)propan-2-one

HRID 49325Notes

Reaction equation

HRID 49325 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7](N(OC)C)=O.[CH2:14]([Mg]Cl)[CH3:15].[OH2:18]>C1COCC1>[Br:1][C:2]1[CH:13]=[C:6]([CH2:7][C:14](=[O:18])[CH3:15])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 184722695-Bromo-N-methoxy-N-methylpyridine-3-carboxamideHCID 178461633HCID 178461633, compound

Product 1

HCID 177501471-(5-Bromopyridin-3-yl)propan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

44 g (180 mmol) of 5-bromo-N-methoxy-N-methylnicotinamide are dissolved in 200 mL of THF and 60 mL (180 mmol) of ethylmagnesium chloride solution (3M in ethyl ether) are added dropwise. The reaction medium is stirred at room temperature for one hour, poured into water and extracted with ethyl acetate. The organic phase is separated out after settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (70/30). 4 g (11%) of 1-(5-bromo-3-pyridyl)propanone are collected.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated out
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (70/30)
  8. custom4 g (11%) of 1-(5-bromo-3-pyridyl)propanone are collected

Sources & evidence

ORD record
ord-dca96e3537174ceca06c1decd22b94ce
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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