Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Benzoic acid, 2-bromo-5-fluoro-, methyl ester | HCID 138875 | — |
| Reactant | 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734652 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 178517107 | HCID 178517107 | 65.8% |
Reaction Steps
A mixture of methyl 2-bromo-5-fluorobenzoate (0.250 g, 1.07 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.235 g, 1.07 mmol), palladium acetate (2.4 mg, 0.01 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (8.81 mg, 0.021 mmol), and sodium carbonate (0.114 g, 1.073 mmol) in ethanol (5.4 mL) was heated to 80° C. for 3 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was triturated with hexane, and isolated by vacuum filtration, washed with water, and dried to provide the title compound (0.15 g, 65% yield) which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08951964B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-f0964649d1874821a3cc4653da2934ea |
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| Source note | uspto-grants-2015_02 |
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