Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Ethynyl-2,4-difluorobenzene | HCID 5063820 | — |
| Reactant | tert-Butyl (2-bromo-4-chlorophenoxy)acetate | HCID 49766393 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 56594263 | HCID 56594263 | — |
Reaction Steps
A solution of tert-butyl(2-bromo-4-chlorophenoxy)acetate (350 mg; 1.09 mmol) and 1-ethynyl-2,4-difluorobenzene (Aldrich, 165 mg; 1.20 mmol) in degassed, anhydrous CH3CN (2.80 mL) was treated with dichlorobis(triphenylphosphine)palladium(II) (38 mg; 0.05 mmol), copper(I) iodide (10 mg; 0.05 mmol) and triethylamine (0.45 mL; 3.26 mmol). The reaction mixture was heated at 50° C. under stirring for 16 hours. The solvent was evaporated and the residue dissolved in DCM (1 mL) and an HCl solution (4 N in dioxane, 2.7 mL) was added. After stirring for 16 hours, the solvents were removed under vacuum and the crude product purified by preparative HPLC. The title compound was obtained as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08273769B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-6129307e2d61465b9dc54076741e185d |
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| Source note | uspto-grants-2012_09 |
|---|
