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

HRID 1024384Notes

Reaction equation

HRID 1024384 reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][C:6]1=[O:12])[CH2:2][CH2:3][CH3:4].P(Br)(Br)([Br:15])=O>CN(C=O)C>[Br:15][C:8]1[CH:9]=[CH:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:12])[CH:7]=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

To a solution of intermediate D2 (1.44 g, 8.6 mmol) in DMF (140 ml) was added phosphorus oxybromide (5.4 g, 18.9 mmol) 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 D3 (1.82 g, 93%).

Workup

  1. temperatureAfter cooling in an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc the combined organic fractions
  4. dry with materialwere 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-47329aca77404725b9d68ec201e5cbf9
Source dataset
uspto-grants-2014_05
Patent number
US08722894B2

Reaction notes

Loading…