Toluene → Methyl 2-(4-fluoroanilino)-4-(3-phenyl-1-propenyl)benzoate

HRID 2191693Notes

Reaction equation

HRID 2191693 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]1[CH:26]=[CH:25][C:12]([NH:13][C:14]2[CH:23]=[C:22](I)[CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1.[CH2:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:28]=[CH2:29]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[F:8][C:9]1[CH:26]=[CH:25][C:12]([NH:13][C:14]2[CH:23]=[C:22]([CH:29]=[CH:28][CH2:27][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 9309AllylbenzeneHCID 57667861Methyl 2-(4-fluoroanilino)-4-iodobenzoate

Product 1

HCID 68959273Methyl 2-(4-fluoroanilino)-4-(3-phenyl-1-propenyl)benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst4×HCID 8471TriethylamineSolvent

Procedure

To toluene 3.0 mL solution of methyl 2-(4-fluoroanilino)-4-iodobenzoate 0.30 g, allylbenzene 0.16 mL and triethylamine 0.11 mL was added palladium acetate 9 mg, and it was heated and refluxed under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, palladium acetate 18 mg was added to it, and it was heated and refluxed under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, palladium acetate 18 mg was added, and it was heated and refluxed under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to room temperature, palladium acetate 18 mg was added, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=20:1] to give methyl 2-(4-fluoroanilino)-4-(3-phenyl-1-propenyl)benzoate.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed under nitrogen atmosphere for 2 hours
  3. temperaturewas heated
  4. temperaturerefluxed under nitrogen atmosphere for 2 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. temperatureit was heated
  7. temperaturerefluxed under nitrogen atmosphere for 1 hour
  8. temperatureAfter the reaction mixture was cooled to room temperature
  9. temperatureit was heated
  10. temperaturerefluxed for 2 hours
  11. temperatureAfter the reaction mixture was cooled to room temperature
  12. filtrationinsoluble matter was filtrated
  13. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a7dfa6b773d54ae6a947b2e3a496c8e4
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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