Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | P-Cresol | HCID 2879 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane | HCID 11618717 | — |
| Reactant | Tert-butyl 2-(benzamido)-4-bromobenzoate | HCID 67343005 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67341701 | HCID 67341701 | — |
Reaction Steps
0.023 mL of p-cresol, 79 mg of tripotassium phosphate, 2.4 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 0.8 mg of palladium acetate were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 1 hour. After the reaction mixture was cooled to room temperature, 4.7 mg of 2-(di-tert-butylphosphino)-2′,4′,6′-triisopropylbiphenyl and 1.7 mg of palladium acetate were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, 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 tert-butyl 2-(benzamido)-4-(4-methylphenoxy)benzoate.
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-7a2ab48b414d4c9c85a65854fa07cb9a |
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| Source note | uspto-grants-2011_08 |
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