Phosphorus oxybromide → 4-bromo-1-butylpyridin-2(1H)-one

HRID 516620Notes

Reaction equation

HRID 516620 reaction equation
P(Br)(Br)([Br:3])=O.[CH2:6]([N:10]1[CH:15]=[CH:14][C:13](O)=[CH:12][C:11]1=[O:17])[CH2:7][CH2:8][CH3:9]>CN(C=O)C>[Br:3][C:13]1[CH:14]=[CH:15][N:10]([CH2:6][CH2:7][CH2:8][CH3:9])[C:11](=[O:17])[CH:12]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 594970761-butyl-4-hydroxy-1H-pyridine-2-one

Product 1

HCID 594970924-bromo-1-butylpyridin-2(1H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Phosphorus oxybromide (5.4 g, 18.9 mmol) was added to a solution of intermediate D5 (1.44 g, 8.6 mmol) in DMF (140 ml) and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath, the solution was partitioned between water and EtOAc. After three extractions with EtOAc, the combined organic fractions were dried (Na2SO4) and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D6 (1.82 g, 93%).

Workup

  1. temperatureAfter cooling in an ice bath
  2. customthe solution was partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-030ec2cc9bb84ba2b21ad726162d1b45
Source dataset
uspto-grants-2015_08
Patent number
US09114138B2

Reaction notes

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