Benzoyl chloride, 2-chloro-5-nitro- → 2-Chloro-5-nitrophenyl 2-furyl ketone

HRID 48964

Reaktionsgleichung

Reaktionsgleichung von HRID 48964
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C([Sn](CCCC)(CCCC)[C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)CCC>O1CCCC1>[O:20]1[CH:21]=[CH:22][CH:23]=[C:19]1[C:4]([C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1])=[O:5]

Komponenten

4

Edukt 2

HCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 43936882-(Tributylstannyl)furan

Produkt 1

HCID 206342572-Chloro-5-nitrophenyl 2-furyl ketoneAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-chloro-5-nitrobenzoyl chloride(5.50 g, 0.0250 mol) and tetrahydrofuran is added 2-tributylstannylfuran (10.1 g, 0.0275 mol) followed by dichloro-bis-triphenylphosphine palladium (0.540 g, 0.00075 mol). The resultant mixture is stirred overnight at room temperature and concentrated in vacuo. The resultant oil is chromatographed on silica gel with methylene chloride-hexanes to afford the title compound as a bright yellow solid (4.95 g, 78.7%, mp 93-96° C.) which is identified by IR and NMR spectral analysis.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe resultant oil is chromatographed on silica gel with methylene chloride-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3f03732945914244a40bb426448167a6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706663B2

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