Potassium Iodide → 2-(2-Methyl-3-trifluoromethyl-phenoxy)-butyronitrile

HRID 455322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 455322
CS([O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8])(=O)=O.[CH3:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][C:13]=1O.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C.O.C(OC)(C)(C)C>[CH3:11][C:12]1[C:17]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:15]=[CH:14][C:13]=1[O:5][CH:6]([CH2:9][CH3:10])[C:7]#[N:8]

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 154676912-(Methanesulfonyloxy)-butyronitrileHCID 201116982-Methyl-3-(trifluoromethyl)phenol

Produkt 1

HCID 670178622-(2-Methyl-3-trifluoromethyl-phenoxy)-butyronitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-(methanesulfonyloxy)-butyronitrile (449 mg, 2.75 mmol), 2-methyl-3-trifluoromethylphenol (440 mg, 2.5 mmol), potassium carbonate (432 mg, 3.13 mmol) and potassium iodide (42 mg, 0.25 mmol) in acetonitrile (20 ml) was stirred overnight at 80° C. The mixture was shaken between tBuOMe and water, washed with NaCl (aq. satd) and the ethereal phase dried with MgSO4 and evaporated. The crude product was chromatographed on silica with EtOAc and hexane to give 2-(2-methyl-3-trifluoromethyl-phenoxy)-butyronitrile. 1H-NMR (CDCl3) 1.20 t, 3H; 2.15 dt, 2H; 2.36 s, 3H; 4.75, t, 2H; 7.17, d, 1H; 7.28, t, 1H; 7.37 d, 1H.

Aufarbeitung

  1. washwashed with NaCl (aq. satd)
  2. dry with materialthe ethereal phase dried with MgSO4
  3. customevaporated
  4. customThe crude product was chromatographed on silica with EtOAc and hexane

Quellen und Nachweise

ORD-Eintrag
ord-dbdf93172c13420ebc420505bb91342d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497293B2

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