HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 67022350, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Hydroxypyrrolidine | HCID 98210 | — |
| Reactant | 4-Bromo-3-fluorobenzotrifluoride | HCID 142414 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67022350 | HCID 67022350 | 66% |
Reaction Steps
A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (4.6 g), 3-hydroxypyrrolidine (1.5 g), palladium(II) acetate (137 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.07 g) and cesium carbonate (16.8 g) in toluene (90 ml) was stirred under an argon gas atmosphere at 85° C. for 16 hr. After cooling to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 90:10-65:35) to give the title compound (2.82 g, yield 66%) as a gray solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338622B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-8c49f0635e4d4670a51aaf406a3f9736 |
| Source note | uspto-grants-2012_12 |