Potassium Fluoride → 5-Bromo-2-(trifluoromethyl)pyrimidine

HRID 512142

Reaktionsgleichung

Reaktionsgleichung von HRID 512142
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[Si]([C:13]([F:16])([F:15])[F:14])(C)(C)C.[F-].[K+]>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:13]([F:16])([F:15])[F:14])=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 70066515-Bromo-2-iodopyrimidine

Produkt 1

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidineAusbeute 16,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-iodo-pyrimidine (30 g, 0.11 mol), TMSCF3 (30 g, 0.21 mol), KF (9.2 g, 0.16 mol) and CuI (30 g, 0.16 mol) in DMF (300 mL) was stirred at room temperature overnight. The reaction mixture was quenched by NH3.H2O (600 mL) and extracted with EtOAc (500 mL×3). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (Petroleum ether) to give 5-bromo-2-trifluoromethyl-pyrimidine (4 g, yield: 16.7%). 1H NMR (CDCl3 400 Hz): δ8.90 (s, 2H).

Aufarbeitung

  1. customThe reaction mixture was quenched by NH3.H2O (600 mL)
  2. extractionextracted with EtOAc (500 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (Petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-a5e49ed79b414c7f9c2e3af28f397992
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102591B2

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