Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Methyl 2-Bromo-5-nitrobenzoate | HCID 245494 | — |
| Reactant | 2,3,4-Trifluorobenzeneboronic acid | HCID 2783280 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58027130 | HCID 58027130 | 53% |
Reaction Steps
A mixture of 2,3,4-trifluorophenylboronic acid (4.70 g, 26.7 mmol), methyl 2-bromo-5-nitrobenzoate (9.02 g, 34.7 mmol), sodium carbonate (8.49 g, 80.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.55 g, 1.34 mmol) was suspended in a mixture of toluene (160 mL)-ethanol (40 mL)-water (80 mL), and then the mixture was stirred under nitrogen atmosphere at 95° C. overnight. After cooling down, ethyl acetate (200 mL) and water (200 mL) were added thereto, and then separated. The organic layer was washed with saturated brine (150 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (4.37 g) as a brown oil. (Yield 53%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08420635B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-c62a98fb9eb74825bbdab28600810dc5 |
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| Source note | uspto-grants-2013_04 |
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