Styrene → HCID 67343131, compound

HRID 2191620Notes

Reaction equation

HRID 2191620 reaction equation
CN(C)C(=O)C.Br[C:8]1[CH:20]=[CH:19][C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([N+:21]([O-:23])=[O:22])[CH:9]=1.[CH2:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C([O-])(=O)C.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[N+:21]([C:10]1[CH:9]=[C:8](/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=[CH:19][C:11]=1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O-:23])=[O:22]

Participants

9

Reactant 4

HCID 7501Styrene2×HCID 31374DimethylacetamideHCID 517045Sodium AcetateHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 67343131HCID 67343131, compound

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalyst2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To N,N-dimethylacetamide 48 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 6.0 g were added styrene 2.7 mL, sodium acetate 2.5 g, tetrabutylammonium bromide 3.2 g and palladium acetate 0.22 g sequentially, and it was heated and stirred under nitrogen atmosphere at 90° C. for 3 hours. After the reaction mixture was cooled to room temperature, styrene 0.45 mL and palladium acetate 0.22 g were added to it, and it was stirred at 110° C. for 3 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, 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 tert-butyl 2-nitro-4-((E)-2-phenylvinyl)benzoate 3.8 g of white solid.

Workup

  1. temperatureit was heated
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. stirringwas stirred at 110° C. for 3 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-96a00275f0e44a0b95184b36e6d87aa2
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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