Dimethylformamide → trans-Stilbene

HRID 368910Notes

Reaction equation

HRID 368910 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CCCC)CCCC)CCC.CN(C=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:2]1(/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7501StyreneHCID 7622TributylamineHCID 11575Iodobenzene

Product 1

HCID 638088trans-StilbeneYield 87%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

Table 1, Entry 3. In the reaction tube were mixed iodobenzene (0.204 g, 1.0 mmol), styrene (0.130 g, 1.25 mmol), palladium acetate (0.00225 g, 0.01 mmol), tri-n-butylamine (0.185 g, 1.0 mmol) and 0.50 ml DMF.under nitrogen. The contents of the flask were irradiated for 2.50 min with an effect of 90 W. After cooling, the product mixture was poured into 25 ml water and was extracted three times with 25 ml DCM. The combined extracts were washed with 25 ml water and concentrated to an oil. The crude product was purified by column chromatography on silica gel using i-hexane as the eluent. The yield was 87% (white crystals, terminal/internal arylation 19/1).

Workup

  1. customThe contents of the flask were irradiated for 2.50 min with an effect of 90 W
  2. temperatureAfter cooling
  3. extractionwas extracted three times with 25 ml DCM
  4. washThe combined extracts were washed with 25 ml water
  5. concentrationconcentrated to an oil
  6. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a5efc1ba290b45f3bfeac6835dd1d7ab
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Reaction notes

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