Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-5-fluorotoluene | HCID 96743 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 67313934 | HCID 67313934 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58677674 | HCID 58677674 | — |
Reaction Steps
2-Bromo-5-fluorotoluene (56 μL, 0.44 mmol) was dissolved in 3 mL dry 1,4-dioxane in a vial under an argon atmosphere. Compound 468 (132 mg, 0.37 mmol) was added and dissolved in the solvent. Rac-BINAP (8.6 mg, 0.014 mmol), Pd2(dba)3 (8.5 mg, 0.009 mmol) and Cs2CO3 (169 mg, 0.52 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 48 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/DCM 1:3 as the eluent to afford the title compound as yellow foam. 13C NMR (CDCl3) δ 195.5, 169.8, 160.7, 150.2, 141.1, 138.1, 137.2, 136.5, 135.7, 134.2, 133.6, 129.7, 129.2, 127.3, 127.3, 123.9, 117.9, 115.2, 113.9, 111.5, 66.9, 48.2, 42.5, 20.2, 18.1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07977387B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-fee20129bf44405ca8c22a7f2d710c9c |
|---|
| Source note | uspto-grants-2011_07 |
|---|