Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2,6-Dichlorophenol | HCID 6899 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N-3-Bromopropylphthalimide | HCID 21611 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 60611463 | HCID 60611463 | 94% |
Reaction Steps
A solution of 2,6-dichlorophenol (500 mg, 3.07 mmol), tetrabutyl ammonium iodide (227 mg, 0.613 mmol) and 2-(3-bromopropyl)isoindoline-1,3-dione (905 mg, 3.37 mmol) was stirred in THF (5 mL) at rt. Cs2CO3 (1.80 g, 5.52 mmol) was added. The resulting mixture was stirred at 50° 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 9A (1010 mg, 2.88 mmol, 94% yield) as a white powder. LC-MS (ESI) 365 (M+H), RT=2.23 min (Method B).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08946430B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-2174d5bf7c7d4fa3859e64e103a65f76 |
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| Source note | uspto-grants-2015_02 |
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