HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Ethyl 2-(4-amino-2-chloro-5-iodophenoxy)-4-fluorobenzoate | HCID 67228200 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 2-(4-amino-2-chloro-5-((trimethylsilyl)ethynyl)phenoxy)-4-fluorobenzoate | HCID 67226491 | — |
Reaction Steps
To a mixture of EXAMPLE 242B (3.0 g), bis(triphenylphosphine)palladium(II) dichloride (242 mg), CuI (66 mg) in triethylamine (30 mL) was added trimethylsilylacetylene (2.2 g). The mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with aqueous NH4Cl, water, brine and dried over Na2SO4. The mixture was filtered, and the solvent was evaporated and the residue was loaded on a column and eluted with 10% ethyl acetate in hexane to give the pure product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303025B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-36193c3b51b848e6a0f41a7f826c2d29 |
| Source note | uspto-grants-2016_04 |