반응 #91531

반응 방정식

ethyl 2-bromo-2,2-difluoroacetate

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

→

title compound

수율 56.5%

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

수율 56.5%

용매

ethyl acetate

dimethylsulfoxide

반응 조건

후처리

1. 1
   온도the mixture heated at 50° C. for 16 h
2. 2
   온도The reaction mixture was cooled to room temperature
3. 3
   workup.STIRRINGstirred for 10 min
4. 4
   여과The mixture was filtered through a plug of Celite®
5. 5
   세척the filtrate was washed with saturated NH4Cl solution
6. 6
   기타to remove any remaining copper
7. 7
   건조The solution was dried (Na2SO4) and solvent
8. 8
   기타was removed under reduced pressure

실험 절차

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]+).

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