HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 2-Fluoro-4-(3-trifluoromethylphenylthio)benzaldehyde
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | 3-(Trifluoromethyl)benzenethiol | HCID 136751 | — |
| Edukt | 4-Bromo-2-fluorobenzaldehyde | HCID 143517 | — |
| Katalysator | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Katalysator | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | 2-Fluoro-4-(3-trifluoromethylphenylthio)benzaldehyde | HCID 58022601 | 68% |
Reaktionsschritte
Under an argon atmosphere, ethyldiisopropylamine (7.0 mL), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (518 mg), xantphos (578 mg), and 3-trifluoromethylthiophenol (3.56 g) were added at room temperature into a solution of 4-bromo-2-fluorobenzaldehyde (4.06 g) in 1,4-dioxane (42 mL), and the resultant solution was heated to reflux for 5 hours. To the reaction solution added water, extracted with ethyl acetate, washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain the target product (4.08 g) as a colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08476305B2 |
| Quelldatensatz | uspto-grants-2013_07 |
| ORD ID | ord-ba81324ddb7f4c3b85a8c5cb1aea8a62 |
| Quellennotiz | uspto-grants-2013_07 |