Triethylamine → HCID 67342987, compound

HRID 1673361Notes

Reaction equation

HRID 1673361 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.[CH:24]([C:26]1[CH:27]=[C:28]([O:32][CH3:33])[CH:29]=[CH:30][CH:31]=1)=[CH2:25].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(OCC)(=O)C>[CH3:33][O:32][C:28]1[CH:27]=[C:26](/[CH:24]=[CH:25]/[C:8]2[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]=2)[CH:31]=[CH:30][CH:29]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31374DimethylacetamideHCID 5841461-Ethenyl-3-methoxybenzeneHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

Product 1

HCID 67342987HCID 67342987, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To 5 mL of N,N-dimethylacetamide solution containing 0.60 g of tert-butyl 4-bromo-2-nitrobenzoate, 0.37 mL of 3-vinylanisole, 0.47 mL of triethylamine and 0.11 g of palladium acetate were added at room temperature and stirred under nitrogen atmosphere at 110° C. for 4 hours. Ethyl acetate and water were added after the reaction mixture was cooled to room temperature. 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 [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=10:1] to obtain 0.20 g of tert-butyl 4-((E)-2-(3-methoxyphenyl)vinyl)-2-nitrobenzoate a pale yellow solid.

Workup

  1. additionwere added at room temperature
  2. temperaturewas cooled to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washafter washed with 10% citric acid aqueous solution
  6. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=10:1]

Sources & evidence

ORD record
ord-c0b3c053a5b34d8180edd86466be45e4
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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