Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Chlorophenyl)boronic acid | HCID 2734323 | — |
| Reactant | tert-Butyl 4-bromo-2-nitrobenzoate | HCID 26369829 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 67343762 | HCID 67343762 | 31.7% |
Reaction Steps
To 20 mL of toluene solution containing 2.0 g of tert-butyl 4-bromo-2-nitrobenzoate, 6.0 mL of ethanol, 3.0 mL of water, 1.2 g of 3-chlorophenylboronic acid, 1.7 g of sodium carbonate and 0.23 g of tetrakis(triphenylphosphine)palladium (0) were added sequentially, and the resulting mixture was heated to reflux under nitrogen atmosphere for 3 hours. Water was added after the reaction mixture was cooled to room temperature. 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 [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=10:1] to obtain 0.70 g of tert-butyl 4-(3-chlorophenyl)-2-nitrobenzoate as white 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-2773fc19cc9047d59b6470eeaf9da2af |
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| Source note | uspto-grants-2011_08 |
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