Reacción #91531

Ecuación de reacción

ethyl 2-bromo-2,2-difluoroacetate

4-((6-Bromopyridin-3-yl)oxy)benzonitrile

→

title compound

Rendimiento 56.5%

ethyl 2-(5-(4-cyanophenoxy)pyridin-2-yl)-2,2-difluoroacetate

Rendimiento 56.5%

Disolventes

ethyl acetate

dimethylsulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture heated at 50° C. for 16 h
2. 2
   TemperaturaThe reaction mixture was cooled to room temperature
3. 3
   workup.STIRRINGstirred for 10 min
4. 4
   FiltraciónThe mixture was filtered through a plug of Celite®
5. 5
   Lavadothe filtrate was washed with saturated NH4Cl solution
6. 6
   Otroto remove any remaining copper
7. 7
   SecadoThe solution was dried (Na2SO4) and solvent
8. 8
   Otrowas removed under reduced pressure

Procedimiento

A mixture of ethyl 2-bromo-2,2-difluoroacetate (22.13 mL, 109.05 mmol) and copper (13.85 g, 218.1 mmol) in dry dimethylsulfoxide (DMSO) (80 mL) was stirred at room temperature (rt) for 4 h. 4-((6-Bromopyridin-3-yl)oxy)benzonitrile (10 g, 36.35 mmol) was added and the mixture heated at 50° C. for 16 h. The reaction mixture was cooled to room temperature, diluted with 200 mL of ethyl acetate (EtOAc) and stirred for 10 min. The mixture was filtered through a plug of Celite® and the filtrate was washed with saturated NH4Cl solution to remove any remaining copper. The solution was dried (Na2SO4) and solvent was removed under reduced pressure to give the title compound as brown oil (6.5 g, 56.5%): IR (thin film) 2229, 1767 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.44 (d, J=2.7 Hz, 1H), 7.78 (d, J=8.7 Hz, 1H), 7.73-7.64 (m, 2H), 7.49 (dd, J=8.6, 2.7 Hz, 1H), 7.16-7.07 (m, 2H), 4.39 (q, J=7.1 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H); ESIMS m/z 319 ([M+H]+).

Fuente