Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-3-fluorophenol | HCID 2779153 | — |
| Reactant | Cyclobutyl 4-methylbenzene-1-sulfonate | HCID 12621595 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 90043208 | HCID 90043208 | — |
Reaction Steps
4-bromo-3-fluorophenol (315 mg, 1.648 mmol), cyclobutyl 4-methyl-benzenesulfonate (373 mg, 1.648 mmol), and cesium carbonate (1074 mg, 3.30 mmol) were dissolved in DMSO (1648 μl) and heated to 60° C. overnight. The reaction mixture was diluted with water and EtOAc. The aqueous phase was extracted with EtOAc (×2) and the combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography on a Biotage™ 50 g column by eluting with 2% to 50% EtOAc:Hexane. 1H NMR δ (ppm) 7.4 (t, 1H), 6.10 (dd, 1H), 6.53 (dd, 1H), 4.60 (quintet, 1H), 2.49-2.43 (m, 2H), 2.21-2.13 (m, 2H), 1.93 (m, 1H), 1.73 (sextet, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09382243B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-824c5e69958e48f094a1b76f7b75cc15 |
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| Source note | uspto-grants-2016_07 |
|---|