Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | 1-Bromo-4-nitrobenzene | HCID 11466 | — |
| Reactant | Tert-butyl 2-(benzamido)-4-vinylbenzoate | HCID 67343635 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 67344729 | HCID 67344729 | 72.8% |
Reaction Steps
0.14 g of 1-bromo-4-nitrobenzene, 0.22 mL of tributylamine and 5.2 mg of palladium acetate were added to 2.0 mL of N,N-dimethylacetamide solution containing 0.15 g of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred under nitrogen atmosphere at 110° C. for 1 hour and 20 minutes. After the reaction mixture was cooled to room temperature, 10% citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution, a saturated sodium thiosulfate 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 [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane:ethyl acetate=4:1]to obtain 0.15 g of tert-butyl 2-(benzamido)-4-((E)-2-(4-nitrophenyl)vinyl)benzoate as yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07999132B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-988a0571df764499baa0ffb3588a172c |
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| Source note | uspto-grants-2011_08 |
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