HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 86658335, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Hydroxypyrrolidine | HCID 98210 | — |
| Reactant | 2,4-Bis(trifluoromethyl)bromobenzene | HCID 136164 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86658335 | HCID 86658335 | 79.6% |
Reaction Steps
A solution of 1-bromo-2,4-bis(trifluoromethyl)benzene (4.45 g), 3-hydroxypyrrolidine (1.2 g), palladium(II) acetate (156 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (846 mg) and cesium carbonate (13.6 g) in toluene (74 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 (3.28 g, yield 79%) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338622B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-6e4da376d8934a3dbcca2304ab0943ff |
| Source note | uspto-grants-2012_12 |