Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tert-Butylamine | HCID 6385 | — |
| Reactant | 4-Bromo-3-(trifluoromethyl)aniline | HCID 67852 | — |
| Reactant | Potassium trifluorovinylborate | HCID 86620274 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | 3-Trifluoromethyl-4-vinylaniline | HCID 23155172 | 79% |
Reaction Steps
4-Bromo-3-(trifluoromethyl)aniline (4.0 g, 16.7 mmol) was dissolved in isopropanol (20 mL), water (10 mL), and t-butylamine (5 mL). To the solution, potassium(trifluoro)vinylborate (4.0 g, 29.9 mmol), PdCl2(dppf)2.2-dichloromethane complex (300 mg, 0.37 mmol) were added. The resulting mixture was stirred under argon atmosphere at 80° C. for 20 hours and then concentrated. The residue was partitioned between water and ethyl acetate, and the organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting product was purified by silica-gel column chromatography (n-hexane:ethyl acetate=6:1) to give 3-trifluoromethyl-4-vinylaniline (2.475 g, 79%) as a light-yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08299252B2 |
|---|
| Source dataset | uspto-grants-2012_10 |
|---|
| ORD ID | ord-6eb1ebd3178146babfd787f8b81ef64f |
|---|
| Source note | uspto-grants-2012_10 |
|---|
