Methyl Acrylate → methyl (E)-3-(4-cyanophenyl)prop-2-enoate

HRID 368909Notes

Reaction equation

HRID 368909 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C=O)C>[CH3:15][O:14][C:10](=[O:13])/[CH:11]=[CH:12]/[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 12162Benzonitrile, 4-bromo-HCID 80271Tri-o-tolylphosphine

Product 1

HCID 11106082methyl (E)-3-(4-cyanophenyl)prop-2-enoateYield 94%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Table 1, Entry 2. In the reaction tube were mixed 4-bromobenzonitrile (0.182 g, 1.0 mmol), methyl acrylate (0.108 g, 1.25 mmol), palladium acetate (0.00225 g, 0.01 mmol), tri-o-tolylphosphine (0.0122 g, 0.04 mmol), triethylamine (0.127 g, 1.25 mmol) and 0.50 ml DMF.under nitrogen. The contents of the flask were irradiated for 3.50 min with an effect of 60 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/diethyl ether (1/1) as the eluent. The yield was 94% (pale yellow crystals).

Workup

  1. customThe contents of the flask were irradiated for 3.50 min with an effect of 60 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-b2631acbf23e41e49ecfa1028c6ba4ee
Source dataset
uspto-grants-2000_10
Patent number
US06136157

Reaction notes

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