Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N-3-Bromopropylphthalimide | HCID 21611 | — |
| Reactant | 2-Trifluoromethylphenol | HCID 67958 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 89862965 | HCID 89862965 | 93% |
Reaction Steps
A solution of 2-(trifluoromethyl)phenol (250 mg, 1.54 mmol), tetrabutyl ammonium iodide (114 mg, 1.31 mmol) and 2-(3-bromopropyl)isoindoline-1,3-dione (455 mg, 1.70 mmol) was stirred in THF (10 mL) at rt. Cs2CO3 (904 mg, 2.78 mmol) was added. The resulting mixture was stirred at 60° C. for 16 h. H2O was added to the reaction mixture and the aqueous layer was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by triturating with Et2O to yield Intermediate 6A (0.50 g, 1.4 mmol, 93% yield) as a white powder. LC-MS (ESI) 350 (M+H), RT=3.41 min (Method B).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09394260B2 |
|---|
| Source dataset | uspto-grants-2016_07 |
|---|
| ORD ID | ord-96e74a2b03544085ac8b8d3ff9c1be94 |
|---|
| Source note | uspto-grants-2016_07 |
|---|