Water → HCID 12873688, compound

HRID 2304449Notes

Reaction equation

HRID 2304449 reaction equation
Br[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[CH2:14].C(N(CC)CC)C.O>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N:18]1[CH:19]=[CH:20][C:15](/[CH:13]=[CH:14]/[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 962WaterHCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80186Ethyl 2-bromobenzoate

Product 1

HCID 12873688HCID 12873688, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

50 g (0.22 mol) of ethyl 2-bromobenzoate, 30 g (0.29 mol) of 4-vinylpyridine and 75 ml (0.54 mol) of triethylamine were dissolved in 750 ml of dimethylformamide. Then 0.36 g of palladium(II) acetate, 0.96 g of tri(o-tolyl)phosphine and 1 ml of water were added and the mixture was refluxed for 3 h. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The organic phase was dried and concentrated in vacuo. The residue was recrystallized [lacuna] cyclohexane/petroleum ether, resulting in 45.3 g (83%) of the product.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized [lacuna] cyclohexane/petroleum ether

Sources & evidence

ORD record
ord-d2189c26959f48aba944b38080d28481
Source dataset
uspto-grants-2002_08
Patent number
US06436925B1

Reaction notes

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