Reaktion #443267

Reaktionsgleichung

2-bromo-4-nitrotoluene

phenyl boric acid

HCl

→

pale orange needles

Ausbeute 57.7%

4-nitro-2-phenyltoluene

Ausbeute 57.7%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with Et2O
2. 2
   SonstigeThe crude material was chromatographed on silica gel
3. 3
   SonstigeAfter recrystallization from ethanol

Vorschrift

2-bromo-4-nitrotoluene (2.16 g, 10.00 mmol) and phenyl boric acid (1.46 g, 12.00 mmol) were dissolved into anhydrous DMF (25 ml) under nitrogen. To this mixture was added Pd(Ph3P)4 (0.58 g, 5%). The mixture was heated at 100° C. overnight. The solution was poured onto 1N HCl and extracted with Et2O. The crude material was chromatographed on silica gel using hexanes as an eluent. After recrystallization from ethanol, 1.23 g (57.6%) of pale orange needles were obtained. mp 69°-71° C.; 1H NMR (CDCl3) 2.36 (3 H, s), 7.29-7.40 (2 H, m), 7.41-7.49 (5 H,m), 8.07-8.10 (2 H, m); 13C NMR (CDCl3) 20.68, 121.96, 124.51, 127.78, 128.41, 128.83, 131.06, 139.44, 142.97, 143.48, 146.05; anal calc. for C13H11NO2 C:73.26, H:5.20, N:6.57; found, C:73.10, H:5.12, N:6.50; m/ z (EI) 213; HRMS calc. for C13H11NO2, 213.0790; found, 213.0793.

Quelle