HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → 4-Bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-Bromo-5-fluoro-2-iodoaniline | HCID 68659476 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-Bromo-5-fluoro-2-[(trimethylsilyl)ethynyl]aniline | HCID 68494805 | — |
Reaction Steps
Triethylamine (44 mL) followed by trimethylsilylacetylene (0.737 mL, 5.32 mmol) were added dropwise to a suspension of 4-bromo-5-fluoro-2-iodoaniline (1.4 g, 4.43 mmol), Pd(PPh3)2Cl2 (0.156 g, 0.222 mmol), and CuI (0.042 g, 0.222 mmol) at 0° C. The reaction was warmed to ambient temperature and stirred for 2 h. The reaction was concentrated, diluted with Et2O, and filtered through Celite. The filtrate was washed with brine, dried (Na2SO4), filtered and concentrated. Chromatography over silica eluting with 2-8% EtOAc/hexanes afforded the desired product as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394969B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-b6051e9ebeb14d998f11fcafa6c574cb |
| Source note | uspto-grants-2013_03 |