3-Nitrostyrene → 3-bromo-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine

HRID 1953402Notes

Reaction equation

HRID 1953402 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[CH2:8])([O-:3])=[O:2].[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](Br)[CH:18]=1.C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](/[CH:8]=[CH:7]/[C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 685143-NitrostyreneHCID 693693,5-DibromopyridineHCID 516892Sodium Bicarbonate2×

Product 1

HCID 232981253-bromo-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-nitrostyrene (5.36 ml), 3,5-dibromopyridine (10.0 g), palladium(II) acetate (259 mg), tetra-n-butylammonium chloride (10.7 g) and sodium bicarbonate (8.07 g) in N,N-dimethylformamide (50 ml) was stirred at 120pbC. for 4 hours. The mixture was poured into sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated. The resultant solid was washed with diisopropyl ether to give 3-bromo-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine (5.74 g).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic solution was washed with sodium bicarbonate solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe resultant solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-86dc2d66d6d54425ad04c5521b2f06ee
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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