Styrene → HCID 67343131, compound

HRID 1673338Notes

Reaction equation

HRID 1673338 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 48 mL of N,N-dimethylacetamide solution containing 6.0 g of tert-butyl 4-bromo-2-nitrobenzoate, 2.7 mL of styrene, 2.5 g of sodium acetate, 3.2 g of tetrabutylammonium bromide and 0.22 g of palladium acetate (II) were added sequentially, and heated and stirred under nitrogen atmosphere at 90° C. for 3 hours. After the reaction mixture was cooled to room temperature, 0.45 mL of styrene and 0.22 g of palladium acetate (II) were added and heated and stirred at 110° C. for 3 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=20:1] to obtain 3.8 g of tert-butyl 2-nitro-4-((E)-2-phenylvinyl)benzoate as white solid.

Workup

  1. additionwere added sequentially
  2. temperatureheated
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. temperatureheated
  5. stirringstirred at 110° C. for 3 hours
  6. temperatureAfter the reaction mixture was cooled to room temperature
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washed with 10% citric acid aqueous solution
  10. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified with silica gel column chromatography [eluent; hexane:ethyl acetate=20:1]

Sources & evidence

ORD record
ord-c82573cc71ff4b56a5acd04600c580ce
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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