반응 #976713

반응 방정식

cesium carbonate

benzyl bromide

5-chloro-2-(trifluoromethyl)benzoic acid

DMA

→

title compound

수율 57.0%

Benzyl 5-cyano-2-(trifluoromethyl)benzoate

수율 57.0%

반응 조건

후처리

1. 1
   농축Concentrate under reduced pressure
2. 2
   workup.ADDITIONadd water
3. 3
   추출extract with EtOAc
4. 4
   기타Separate the organic phase
5. 5
   세척wash with saturated aqueous NaCl
6. 6
   건조dry over MgSO4
7. 7
   여과filter
8. 8
   농축concentrate under reduced pressure

실험 절차

Under a nitrogen atmosphere, to a solution of 5-chloro-2-(trifluoromethyl)benzoic acid (5.02 g, 22.35 mmol, 1.0 equiv) in DMA (45 mL), add zinc(II) cyanide (1.77 g, 15.07 mmol, 0.67 equiv), zinc dust (<10 μM, 330 mg, 5.05 mmol, 0.23 equiv), and bis(tri-tert-butylphosphino)palladium (540 mg, 1.06 mmol, 0.05 equiv). Stir the mixture under a nitrogen atmosphere at 95° C. for 9.5 hours. Add cesium carbonate (13.3 g, 40.82 mmol, 1.83 equiv), then benzyl bromide (3.0 mL, 25.15 mmol, 1.13 equiv), and stir under air at room temperature for 3.5 hours. Concentrate under reduced pressure, add water, and extract with EtOAc. Separate the organic phase and wash with saturated aqueous NaCl, dry over MgSO4, filter, and concentrate under reduced pressure. Subject the resulting crude material to flash chromatography on silica gel eluting with a 0-50% EtOAc/hexanes gradient to give the title compound (3.9 g, 57%). MS (m/z) 306 (M+1).

출처