Dimethylformamide → 4-(Pentafluoroethyl)benzonitrile

HRID 19770

Reaktionsgleichung

Reaktionsgleichung von HRID 19770
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:19])([F:18])[C:12]([F:17])([F:16])C([O-])=O.[Na+].CN(C=O)C>[Cu]I.C1(C)C=CC=CC=1>[F:16][C:12]([F:17])([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:11]([F:19])([F:18])[F:10]

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 764674-IodobenzonitrileHCID 2733305Sodium pentafluoropropionate

Produkt 1

HCID 147741854-(Pentafluoroethyl)benzonitrileAusbeute 52,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 4-iodobenzonitrile (10.0 g, 43.7 mmol), sodium pentafluoroproprionate (15.4 g, 82.9 mmol), and copper(I) iodide (16.6 g, 87.3 mmol), DMF (160 mL), and toluene (60 mL) was heated at 160° C. for 16 h, allowing most of the toluene to distil off. After cooling, ethyl acetate (200 mL) was added, and the mixture was filtered through diatomaceous earth, and the filtrate was partitioned between ethyl acetate/heptane and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (5.05 g 52%). Yellow oil, MS (EI) 221.1 (M+).

Aufarbeitung

  1. customto distil off
  2. temperatureAfter cooling
  3. additionethyl acetate (200 mL) was added
  4. filtrationthe mixture was filtered through diatomaceous earth
  5. customthe filtrate was partitioned between ethyl acetate/heptane and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ffd08d2350414257bcb2b75fcce9e152
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745477B2

Verknüpfte Notizen

Wird geladen…