تفاعل #976713

معادلة التفاعل

cesium carbonate

benzyl bromide

5-chloro-2-(trifluoromethyl)benzoic acid

DMA

→

title compound

المردود 57.0%

Benzyl 5-cyano-2-(trifluoromethyl)benzoate

المردود 57.0%

ظروف التفاعل

المعالجة

1. 1
   تركيزConcentrate under reduced pressure
2. 2
   workup.ADDITIONadd water
3. 3
   استخلاصextract with EtOAc
4. 4
   أخرىSeparate the organic phase
5. 5
   غسيلwash with saturated aqueous NaCl
6. 6
   تجفيفdry over MgSO4
7. 7
   ترشيحfilter
8. 8
   تركيزconcentrate under reduced pressure

الإجراء التجريبي

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).

المصدر