Ammonia → 3,5-Dibromo-2-(trifluoromethyl)pyridine

HRID 1892224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1892224
I[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[F-].[K+].[F:12][C:13]([Si](C)(C)C)([F:15])[F:14].N>CN1C(=O)CCC1.[Cu]I>[Br:8][C:7]1[C:2]([C:13]([F:15])([F:14])[F:12])=[N:3][CH:4]=[C:5]([Br:9])[CH:6]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 269675523,5-Dibromo-2-iodopyridine

Produkt 1

HCID 110449423,5-Dibromo-2-(trifluoromethyl)pyridineAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-iodo-3,5-dibromopyridine (4.21 g, 11.60 mmol) in NMP (25 mL) were added copper(I) iodide (4.42 g, 23.21 mmol), potassium fluoride (1.35 g, 23.21 mmol), and (trifluoromethyl)trimethylsilane (5.61 mL, 35.90 mmol). The resulting mixture was allowed to stir overnight at 50° C. The mixture was poured into 12% aqueous ammonia, and then extracted with Et2O (2×120 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3,5-dibromo-2-(trifluoromethyl)pyridine (1.63 g, 46%) as a liquid.

Aufarbeitung

  1. extractionextracted with Et2O (2×120 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-65350ca69df54dc88472cff7230cbbf0
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507667B2

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