Toluene → Tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate

HRID 1673340Notes

Reaction equation

HRID 1673340 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH2:47]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH:48]=[CH2:49]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[N+:22]([C:11]1[CH:10]=[C:9]([CH:49]=[CH:48][CH2:47][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:21]=[CH:20][C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 1140TolueneHCID 9309AllylbenzeneHCID 80271Tri-o-tolylphosphineHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 67344218Tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst2×HCID 8471TriethylamineSolvent

Procedure

19 mg of palladium acetate (II) was added to 5 mL of toluene solution containing 0.50 g of tert-butyl 4-bromo-2-nitrobenzoate, 50 mg of tri(o-tolyl)phosphine, 0.44 mL of allylbenzene and 0.46 mL of triethylamine, and the resulting mixture was heated to reflux under nitrogen atmosphere for 2 hours. After the reaction mixture was cooled to room temperature, 20 mg of palladium acetate (II) was added and the resulting mixture was heated to reflux for 7 hours. After the reaction mixture was cooled to room temperature, Insoluble were removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=30:1] to obtain 0.31 g of tert-butyl 2-nitro-4-(3-phenyl-1-propenyl)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 2 hours
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 7 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customInsoluble were removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=30:1]

Sources & evidence

ORD record
ord-f30d84118b7244b59201d547ae838736
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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