Triphenylphosphine → 2-Chloro-4-(methylsulfanyl)benzaldehyde
Reaktionsgleichung
[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O.[B-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu+]>[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of 2-chloro-4-(methylsulphenyl)-benzoyl chloride (1.0 g), triphenyl phosphine (2.47 g) and bis(triphenylphosphine)copper (I) borohydride (1.0 g) in acetone was stirred at 0° C. for 1 hour. Further bis (triphenylphosphine)copper (I) borohydride (1.5 g) was added and the mixture was stirred for 2 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and treated with copper (I) bromide (2.1 g). The filtrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of ethyl acetate and hexane to give 2-chloro-4-(methylsulphenyl)benzaldehyde (0.83 g) as an off-white solid, m.p. 76°-77° C.
Aufarbeitung
- stirringthe mixture was stirred for 2 hours
- filtrationThe mixture was filtered
- customthe filtrate was evaporated to dryness
- dissolutionThe residue was dissolved in chloroform
- additiontreated with copper (I) bromide (2.1 g)
- customThe filtrate was evaporated to dryness
- customthe residue was purified by chromotography
- washeluted with a mixture of ethyl acetate and hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-de0b613f9c7a4e388cb4e332f62074ae
- Quelldatensatz
- uspto-grants-1994_11
- Patentnummer
- US05366957
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