반응 #507280

반응 방정식

4-iodobenzotrifluoride

anilinium hypophosphite

3-aminopropyl triethoxysilane

1,3-bis(diphenylphosphino)propane

→

ethyl 4-(trifluoromethyl)phenylphosphinate

수율 28.0%

용매

ethyl acetate

hydrochloric acid

acetonitrile

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도under reflux for 32 hrs
3. 3
   기타partitioned
4. 4
   추출The aqueous layer was further extracted with ethyl acetate
5. 5
   세척the combined extracts were washed with aqueous sodium hydrogen carbonate and brine
6. 6
   건조dried over magnesium sulfate
7. 7
   기타The solvent was removed in vacuo
8. 8
   기타the residue was purified by column chromatography
9. 9
   기타Further purification
10. 10
    workup.DISTILLATIONby distillation
11. 11
    기타afforded compound AZ1 (1.14 g) in 28% yield

실험 절차

To a degassed solution of 4-iodobenzotrifluoride (4.70 g, 17.2 mmol), anilinium hypophosphite (3.51 g, 22.1 mmol), and 3-aminopropyl triethoxysilane (4.88 g, 22.1 mmol) in anhydrous acetonitrile (110 mL) were added palladium acetate (82.5 mg, 0.367 mmol, 2 mol %) and 1,3-bis(diphenylphosphino)propane (167 mg, 0.404 mol, 2.2 mol %). The mixture was heated under reflux for 32 hrs, then cooled down to room temperature, diluted with ethyl acetate and hydrochloric acid (IM) and partitioned. The aqueous layer was further extracted with ethyl acetate, and the combined extracts were washed with aqueous sodium hydrogen carbonate and brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by column chromatography using 25 to 100% ethyl acetate in petroleum ether. Further purification by distillation afforded compound AZ1 (1.14 g) in 28% yield.

출처