Toluene → HCID 67344875, compound

HRID 1673342Notes

Reaction equation

HRID 1673342 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.[C:47]1([CH2:53][CH2:54][CH:55]=[CH2:56])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>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:56]=[CH:55][CH2:54][CH2:53][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=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 130333-ButenylbenzeneHCID 80271Tri-o-tolylphosphineHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 67344875HCID 67344875, compound

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, 0.50 mL of 4-phenyl-1-butene and 0.46 mL of triethylamine, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours and 30 minutes. 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 5 hours and 30 minutes. After cooled to room temperature, the reaction mixture was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=30:1] to obtain 0.35 g of tert-butyl 2-nitro-4-(4-phenyl-1-butenyl)benzoate.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux under nitrogen atmosphere for 4 hours and 30 minutes
  3. temperaturethe resulting mixture was heated
  4. temperatureto reflux for 5 hours and 30 minutes
  5. temperatureAfter cooled to room temperature
  6. customthe reaction mixture was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=30:1]

Sources & evidence

ORD record
ord-a4e3fcb0be414283b799e9e6603eda21
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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