HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehyde → 4-Chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(4-Chloro-3-trifluoromethyl-phenoxy)-3-fluoro-benzaldehyde | HCID 86666198 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Methyltriphenyliphosphonium bromide | HCID 74505 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-Chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether | HCID 67774659 | 80.5% |
Reaction Steps
To a suspension of methyltriphenylphosphonium bromide (6.73 g, 18.83 mmol) in anhydrous THF (20 mL) was added dropwise n-butyllithium (11.77 mL, 18.83 mmol) under −78° C. over 30 min. It was stirred for 1 h, then was added by 4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorobenzaldehyde (5.0 g, 15.69 mmol). It was warmed slowly to room temperature and stirred for overnight at room temperature. Purification via a flash column chromatography then afforded the title compound (4.0 g, 80% yield). LCMS: rt=5.7 min, [M+H+]=316
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08637536B2 |
| Source dataset | uspto-grants-2014_01 |
| ORD ID | ord-942b0b6716854023aa78078cf7e37a1d |
| Source note | uspto-grants-2014_01 |