Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2-Ethylphenylboronic Acid (contains varying amounts of Anhydride) | HCID 4100862 | — |
| Reactant | Methyl 4-bromo-3-(trifluoromethyl)benzoate | HCID 10891333 | — |
| Reactant | 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl | HCID 11269872 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butyl methyl ether | HCID 15413 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66718378 | HCID 66718378 | — |
Reaction Steps
A mixture of methyl 4-bromo-3-(trifluoromethyl)benzoate (3.0 g, 10.6 mmol), 2-ethylphenylboronic acid (2.38 g, 15.9 mmol), cesium fluoride (4.83 g, 31.8 mmol), palladium acetate (48 mg, 0.21 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (261 mg, 0.64 mmol) was prepared in dioxane (30 mL) and water (15 mL), and then heated at 90° C. for 2.5 hours. The reaction mixture was diluted with MTBE (150 mL) and washed with water (50 mL) and brine (50 mL). The aqueous layers were extracted with MTBE (75 mL). The organic layers were combined, dried (MgSO4) and concentrated under vacuum. After purification by flash chromatography (silica, heptane/EtOAc), the title compound was obtained as a colorless oil (3.05 g, 93%). HPLC (Method A) Rt 5.6 min (Purity: 97.3%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08802704B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-e94efb440183407385c95b0759e5004e |
|---|
| Source note | uspto-grants-2014_08 |
|---|