Sodium Iodide → Ethyl 3-phenylprop-2-enoate

HRID 1194572Notes

Reaction equation

HRID 1194572 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[CH:30]=[CH2:31].CCN(CC)CC>CN(C=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].CCOCC>[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[CH:30]=[CH:31][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 5238Sodium IodideHCID 7964ChlorobenzeneHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 11776Triphenylphosphine2×

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoateYield 39%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Chlorobenzene (2825 mg, 25 mmoles), NiBr2 (1095 mg, 5 mmoles), NaI(4125 mg, 27.5 mmoles) and PPh3 (2620 mg, 10 mmoles) were mixed in DMF (20 ml) and heated in 40° C. oil bath for 5 h. The mixture was cooled and treated with ethyl acrylate (2750 mg, 27.5 mmoles), Et3N (2778 mg, 27.5 mmoles), palladium diacetate (56 mg, 0.25 mmoles), and PPh3 (262 mg, 1 mmole). The mixture was heated in a 140° C. oil bath for 18 h. The crude reaction mixture was mixed with Et2O, filtered and washed three times with 50 ml of water. The organic fraction was dried over MgSO4, the solvent was removed on the rotary evaporator and the residue purified by radial chromatography (5:1 volume mixture of hexane and Et2O, two purifications) to give 1700 mg (39% isolated yield) of ethyl cinnamate as a light yellow oil.

Workup

  1. temperatureThe mixture was cooled
  2. temperatureThe mixture was heated in a 140° C. oil bath for 18 h
  3. customThe crude reaction mixture
  4. filtrationfiltered
  5. washwashed three times with 50 ml of water
  6. dry with materialThe organic fraction was dried over MgSO4
  7. customthe solvent was removed on the rotary evaporator
  8. customthe residue purified by radial chromatography (5:1 volume mixture of hexane and Et2O, two purifications)

Sources & evidence

ORD record
ord-ef3b40f1fe714802833de2821d466679
Source dataset
uspto-grants-1989_03
Patent number
US04814489

Reaction notes

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