HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 5-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-Fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde | HCID 86666214 | — |
| Catalyst | Methyltriphenyliphosphonium bromide | HCID 74505 | — |
| Product | 5-(2-Fluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine | HCID 67776690 | 27.2% |
Reaction Steps
To a stirred suspension of 3-fluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)benzaldehyde (2 g, 6.99 mmol) and methyltriphenylphosphonium bromide (2.496 g, 6.99 mmol) in dry THF (40 mL) was added NaH (0.978 g, 24.46 mmol) under nitrogen at 0° C. The mixture was stirred at room temperature for 4 h. The organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (540 mg, 1.900 mmol, 27.2% yield). LCMS: rt=3.65 min, [M+H+]=285
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-2183919669b74a2192a30435a2abf4bc |
| Source note | uspto-grants-2014_01 |