Reaktion #158068

Reaktionsgleichung

4-bromo-2-fluorobenzyl cyanide

3-chlorobenzeneboronic acid

K2CO3

→

2-(3′-chloro-3-fluorobiphenyl-4-yl)acetonitrile

Ausbeute 87.6%

Lösungsmittel

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is cooled to room temperature
2. 2
   SonstigeThe two phases are separated
3. 3
   WaschenThe organic layer is washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 70:30)

Vorschrift

A suspension of 4-bromo-2-fluorobenzyl cyanide (3.50 g, 16.35 mmol), 3-chlorobenzeneboronic acid (2.68 g, 17.17 mmol), Pd(OAc)2 (0.110 g, 0.491 mmol), K2CO3 (5.65 g, 40.9 mmol) and tetrabutylammonium bromide (5.80 g, 17.99 mmol) in water (14 ml) is allowed to stir under nitrogen at 70° C. for 1 hour. The reaction mixture is cooled to room temperature, and diluted with EtOAc. The two phases are separated. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 70:30) to give 2-(3′-chloro-3-fluorobiphenyl-4-yl)acetonitrile (3.52 g); HPLC retention time=1.17 minutes (condition B); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.81 (s, 2 H) 7.29-7.45 (m, 5 H) 7.50-7.55 (m, 2 H).

Quelle