HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde → 2-(2-Fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde | HCID 86666213 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Methyltriphenyliphosphonium bromide | HCID 74505 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 2-(2-Fluoro-4-vinylphenoxy)-6-(trifluoromethyl)pyridine | HCID 67776276 | 50.8% |
Reaction Steps
To a solution of methyltriphenylphosphonium bromide (1226 mg, 3.43 mmol) in THF (15 mL) was added n-BuLi (2.145 mL, 3.43 mmol), stirred for 10 min. then 3-fluoro-4-((6-(trifluoromethyl)pyridin-2-yl)oxy)benzaldehyde (0.691 mL, 3.12 mmol) was added. The mixture was stirred at 0° C. for 1 h, then at room temperature for another 2 h. The reaction mixture was diluted with EA, washed with water, brine (50 mL), and concentrated. The residue was purified via flash chromatography to afford the title compound (449 mg, 49.8% yield) as colorless oil. LCMS: rt=3.13 min
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09174968B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-887c4acb0251413598f0df6cdd0d9304 |
| Source note | uspto-grants-2015_11 |