4-Fluoro-3-methylbenzonitrile → 3-Methyl-4-(methylsulfanyl)benzonitrile

HRID 527372Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527372
[CH3:1][S-:2].[Na+].F[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[CH3:13]>CN(C=O)C>[CH3:13][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:5]=1[S:2][CH3:1])[C:9]#[N:10]

Komponenten

4

Edukt 2

HCID 27791804-Fluoro-3-methylbenzonitrileHCID 4378561Sodium methanethiolate

Produkt 1

HCID 578566063-Methyl-4-(methylsulfanyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Sodium methanethiolate (1.60 g, 22.8 mmol) is added to a solution of 4-fluoro-3-methyl-benzonitrile (2.50 g, 18.5 mmol) in DMF, and the mixture is heated at 80° C. for 15 min. All volatiles are evaporated, and the residue is treated with water. The mixture is extracted with ethyl acetate twice, and the organic layer is dried over Na2SO4 and concentrated. Yield: 3.0 g (99% of theory); ESI mass spectrum: [M+H]+=164; r.t. HPLC: 0.61 min (X011_S03).

Aufarbeitung

  1. customAll volatiles are evaporated
  2. additionthe residue is treated with water
  3. extractionThe mixture is extracted with ethyl acetate twice
  4. dry with materialthe organic layer is dried over Na2SO4
  5. concentrationconcentrated
  6. customr.t
  7. custom0.61 min (X011_S03)

Quellen und Nachweise

ORD-Eintrag
ord-7407de6ace15485596ad83621c5bd3c0
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346794B1

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