Sodium Iodide → 1-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

HRID 524109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 524109
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]Br.[Na+].[I-].[C:13]([S-:15])#[N:14].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][N:14]=[C:13]=[S:15]

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 516872Potassium thiocyanateHCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

Produkt 1

HCID 866548501-Bromo-4-fluoro-2-(isothiocyanatomethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-bromo-2-(bromomethyl)-4-fluorobenzene (12, 5.36 g, 20.0 mmol) in dry DMF (20 mL) was added NaI (1.20 g, 8.00 mmol) and KSCN (3.88 g, 40.0 mmol). The mixture was heated under N2 at 80° C. for 12 h. After cooling to RT, the mixture was diluted with water (100 mL), and extracted with EtOAc (50 mL×2). The combined extracts were washed with brine, dried over MgSO4 and concentrated to give crude product. This was purified by column chromatography on silica gel, and eluted with petroleum ether to provide 1-bromo-4-fluoro-2-(isothiocyanatomethyl)benzene (13).

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. extractionextracted with EtOAc (50 mL×2)
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThis was purified by column chromatography on silica gel
  8. washeluted with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-f862176ba1de4decb4fff9c24c3e80b1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340523B2

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