Reaktion #2281980

ord-0e9d719902e241899b1fc247c6c33709

Reaktionsgleichung

COc1cc(C)cc(Br)c1
1-bromo-3-methoxy-5-methyl-benzene
CN(C)C=O
DMF
COc1cc(C)cc(C#N)c1
solid
Ausbeute 83.0%
COc1cc(C)cc(C#N)c1
3-Methoxy-5-methyl-benzonitrile
Ausbeute 83.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
90°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenby washing with brine
  2. 2
    EinengenThe organic layer was concentrated
  3. 3
    Sonstigepurified (silica gel, 0-50% EtOAC/hexane)

Vorschrift

In a 100 mL round bottom flask, 1-bromo-3-methoxy-5-methyl-benzene (2.17 g, 10.79 mmol), Zn(CN)2 (1.9 g, 16.19 mmol, 1.5 eq.) and Pd(PPh3)4 (1.24 g, 1.08 mmol, 0.1 eq.) was charged with DMF (20 mL). The reaction mixture was heated at 90° C. under Ar for 7 hours. Ethyl acetate was added, followed by washing with brine. The organic layer was concentrated and purified (silica gel, 0-50% EtOAC/hexane) to give a white solid (1.31 g, 83%). 1H NMR (300 MHz, CDCl3): δ 7.05 (s, 1H), 6.97 (s, 2H), 3.81 (s, 3H), 2.39 (s, 3H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08334295B2uspto-grants-2012_12