Reaktion #507153

Reaktionsgleichung

2-methyl-2-(4-methylphenyl)propanenitrile

DMF

→

4-(1-cyano-1-methylethyl)benzonitrile

Ausbeute 85.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe solid recovered by filtration
2. 2
   workup.DISSOLUTIONThe solid residue is dissolved in methanol
3. 3
   Filtrationfiltered
4. 4
   Sonstigeto remove insoluble impurities
5. 5
   Einengenconcentrated under vacuo
6. 6
   Sonstigepurified by normal phase MPLC (SiO2, hexane to EtOAc)

Vorschrift

2-methyl-2-(4-methylphenyl)propanenitrile (3.51 g, 15.7 mmol) is dissolved in dry DMF (10 mL). Zn(CN)2 (2.02 g, 17.2 mmol) and Pd(PPh3)4 (906 mg, 5 mol %) are added and the mixture heated at 100° C. for 3 hours. The reaction mixture is diluted with water and the solid recovered by filtration. The solid residue is dissolved in methanol, filtered to remove insoluble impurities, concentrated under vacuo and purified by normal phase MPLC (SiO2, hexane to EtOAc), giving 4-(1-cyano-1-methylethyl)benzonitrile (2.28 g, 13.4 mmol, 85%) as a white solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.70 (s, 6H) 7.73 (dt, J=8.64, 2.03 Hz, 2H) 7.92 (dt, J=8.69, 2.00 Hz, 2H).

Quelle