Methyl 4-bromobenzoate → HCID 18950661, compound

HRID 1492551Notes

Reaction equation

HRID 1492551 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:10])[CH:8]=[CH2:9])[CH:2]=1.Br[C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:10]=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:8][CH2:9][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 12081Methyl 4-bromobenzoateHCID 11389412HCID 11389412, compound

Product 1

HCID 18950661HCID 18950661, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1-(3-Pyridyl)-2-propen-1-ol (1.36 g), methyl p-bromobenzoate (1.44 g) and palladium acetate II (0.02 g) were dissolved in 30 ml of N,N-dimethylformamide, and stirred under heating at 120° C. overnight. The obtained reaction mixture was concentrated, to which was poured water and extracted with ethyl acetate. The extract with ethyl acetate was washed in saturated aqueous sodium chloride solution and dried over magnesium sulfate. The residue was subjected to chromatography on a silica gel column, which was eluted with chloroform-methanol (20:1 v/v), to obtain 1.25 g of methyl 4-[3-oxo-3-(3-pyridyl)propyl]benzoate.

Workup

  1. customThe obtained reaction mixture
  2. concentrationwas concentrated, to which
  3. additionwas poured water
  4. extractionextracted with ethyl acetate
  5. extractionThe extract with ethyl acetate
  6. washwas washed in saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. washwas eluted with chloroform-methanol (20:1 v/v)

Sources & evidence

ORD record
ord-98b29a97eeae4d66ba889e3b559096a4
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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