3-Nitrostyrene → HCID 22724370, compound

HRID 2086814Notes

Reaction equation

HRID 2086814 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].[Cl:12][C:13]1[CH:18]=[C:17](I)[CH:16]=[C:15]([Cl:20])[CH:14]=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>[Cl:12][C:13]1[CH:18]=[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:16]=[C:15]([Cl:20])[CH:14]=1

Participants

7

Reactant 3

HCID 685143-NitrostyreneHCID 764241,3-Dichloro-5-iodobenzeneHCID 516892Sodium Bicarbonate2×

Product 1

HCID 22724370HCID 22724370, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
110 °C

Procedure

A mixture of 3-nitrostyrene (4.6 ml), 1,3-dichloro-5-iodobenzene (7.8 g), palladium(II) acetate (0.20 g), tetrabutylammonium chloride (8.4 g) and sodium bicarbonate (6.3 g) in N,N-dimethylformamide (40 ml) was stirred at 110° C. for 4 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 1,3-dichloro-5-[(E)-2-(3-nitrophenyl)vinyl]benzene (7.93 g).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-f49a0a82be06401a84268efb048d77f6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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