Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-5-fluorotoluene | HCID 96743 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 67314102 | HCID 67314102 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11282738 | HCID 11282738 | — |
Reaction Steps
2-Bromo-5-fluorotoluene (47 μL, 0.37 mmol) was dissolved in 3 mL dry 1,4-dioxane in a vial under an argon atmosphere. Compound 404 (110 mg, 0.31 mmol) was added and dissolved in the solvent. Rac-BINAP (7.3 mg, 0.012 mmol), Pd2(dba)3 (7.0 mg, 0.008 mmol) and Cs2CO3 (141 mg, 0.43 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 72 h. The reaction mixture was filtered and then purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) (v:v=0:100 to 50:50) as the eluent to afford the title compound as brown oil. 13C NMR (CDCl3) δ 195.4, 169.7, 160.6, 150.3, 139.8, 139.7, 136.6, 135.4, 134.0, 133.7, 132.4, 131.5, 129.2, 127.9, 127.4, 127.0, 117.8, 115.0, 113.8, 111.7, 66.8, 48.3, 42.8, 20.2, 18.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07977387B2 |
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| Source dataset | uspto-grants-2011_07 |
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| ORD ID | ord-322a210984154680aa1dde8a4a246dd4 |
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| Source note | uspto-grants-2011_07 |
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