2-Chloro-3-methyl-5-nitropyridine → 2-Fluoro-3-methyl-5-nitropyridine

HRID 3315

Reaktionsgleichung

Reaktionsgleichung von HRID 3315
Cl[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[F-:12].[K+]>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C.CCOCC>[F:12][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Komponenten

6

Edukt 2

HCID 896482-Chloro-3-methyl-5-nitropyridineHCID 522689Potassium Fluoride

Produkt 1

HCID 124081842-Fluoro-3-methyl-5-nitropyridineAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2724163Tetraphenylphosphonium BromideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol; from Maybridge Chemical Co.), KF (12 g, 258 mmol) and tetraphenylphosphonium bromide (20 g, 47.7 mmol; Aldrich) were combined in 200 mL of acetonitrile and heated at reflux for 4 days. The mixture was diluted with Et2O (500 mL) and filtered, and the filtrate was concentrated. The residue was triturated with hot hexane (4×200 mL), and the hexane solutions were combined and concentrated to afford the title compound as a solid (8.4 g, 60%): 1H NMR (DMSO-d6, 300 MHz) δ2.42 (s, 3H), 8.43 (m, 1H), 8.95 (dd, J=1.6 Hz, 1H); MS (CI/NH3) m/z: 157 (M+H)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 4 days
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was triturated with hot hexane (4×200 mL)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2530436b50534fbdbbf72c2ea6ad27e3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733912

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