HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 86658338, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Hydroxypyrrolidine | HCID 98210 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2,5-Bis(trifluoromethyl)bromobenzene | HCID 2734763 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86658338 | HCID 86658338 | 92% |
Reaction Steps
A solution of 2,5-bis(trifluoromethyl)phenyl bromide (4.45 g), 3-hydroxypyrrolidine (1.2 g), palladium(II) acetate (0.16 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.87 g) and cesium carbonate (13.6 g) in toluene (74 mL) was stirred under an argon gas atmosphere at 80° C. for 16 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract 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 90:10-75:25) to give the title compound (3.79 g, yield 91%) as an orange oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338622B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-2a41ef61ab174745bb2c53c77dbfae65 |
| Source note | uspto-grants-2012_12 |