반응 #158068

반응 방정식

4-bromo-2-fluorobenzyl cyanide

3-chlorobenzeneboronic acid

K2CO3

→

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

수율 87.6%

용매

EtOAc

water

반응 조건

후처리

1. 1
   온도The reaction mixture is cooled to room temperature
2. 2
   기타The two phases are separated
3. 3
   세척The organic layer is washed with brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 70:30)

실험 절차

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).

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