HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 46941681, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1-Bromo-3,5-bis(trifluoromethyl)benzene | HCID 67602 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | (3R)-pyrrolidin-3-ol hydrochloride | HCID 2759336 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 46941681 | HCID 46941681 | 61.3% |
Reaction Steps
A mixed solution of 3,5-bis(trifluoromethyl)phenyl bromide (22.0 g), (R)-3-hydroxypyrrolidine hydrochloride (9.23 g), palladium(II) acetate (0.84 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.68 g) and cesium carbonate (73.4 g) in toluene (300 mL)-1,4-dioxane (100 mL) was stirred under an argon gas atmosphere at 80° C. for 16 hr. The solid was filtered off, and the filtrate was washed with saturated brine and water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate 10:1-3:1) to give the title compound (13.7 g, yield 61%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08338622B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-8e1b22883bff4de7862624238c24287d |
| Source note | uspto-grants-2012_12 |