Sodium Azide → (2-Azido-3-fluoro-propyl)benzene

HRID 749298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749298
CS(O[CH:6]([CH2:14][F:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)=O.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.O.[Cl-].[Na+].O>[N:16]([CH:6]([CH2:14][F:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[N+:17]=[N-:18]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 866014541-Fluoromethyl-2-phenylethyl methanesulfonate

Produkt 1

HCID 22054864(2-Azido-3-fluoro-propyl)benzeneAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 1-fluoromethyl-2-phenylethyl methanesulfonate (1.1 g) in anhydrous DMF (15 mL) under nitrogen was added sodium azide (0.53 g) followed by heating at 80° C. overnight. The cooled reaction mixture was diluted with equal parts of water and brine and extracted with EtOAc. The extracts were washed with water and brine, dried over Na2SO4, and concentrated to an oil which was chromatographed over silica gel with a mixture of EtOAc and hexane to give 0.70 g of the title compound. MS ES (M++H−N2) 151.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. washThe extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil which
  6. customwas chromatographed over silica gel with a mixture of EtOAc and hexane

Quellen und Nachweise

ORD-Eintrag
ord-1309630df0844a67ae1270f40a353ec4
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402604B2

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