Acetonitrile → 2-Fluoro-5-nitropyridine

HRID 367052

Reaktionsgleichung

Reaktionsgleichung von HRID 367052
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[F-:11].[K+].C(#N)C>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>[F:11][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 6342AcetonitrileHCID 783082-Chloro-5-nitropyridine2×HCID 522689Potassium Fluoride

Produkt 1

HCID 952642-Fluoro-5-nitropyridineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724163Tetraphenylphosphonium BromideKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2-Chloro-5-nitropyridine (100 g, 0.656 mol, Aldrich), potassium fluoride (84.1 g, 1.45 mol, Aldrich), tetraphenylphosphonium bromide (95.3 g, 0.227 mol, Aldrich), and acetonitrile (1.5 L) were combined and heated at reflux until consumption of the 2-chloro-5-nitropyridine was complete. The volume of the mixture was reduced to 750 mL, diluted with 2 L of ether, filtered and concentrated. The resultant residue was triturated with hot hexane, and the combined hexane extracts were concentrated to give of the title compound (48 g, 54%): 1H NMR (CDCl3, 300 MHz) δ 7.15 (dd, J=3, 6 Hz, 1H), 8.64 (m, 1H), 9.15 (d, J=1.6 Hz, 1H).

Aufarbeitung

  1. temperatureheated
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe resultant residue was triturated with hot hexane
  5. concentrationthe combined hexane extracts were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-15c08ec3a41c4b66a02a81bb36bd2c99
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06133253

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