反应详情

To a stirred and ice-cooled solution of potassium tert-butoxide (0.432 g, 3.6566 mmol) in tert-butanol (15 ml), commercial 4-acetamidophenylacetonitrile (0.5096 g, 2.9252 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.500 g, 2.4377 mmol) are added under a nitrogen atmosphere and the reaction mixture is allowed to attain spontaneously room temperature (1 h) and finally refluxed for 6 h. The resulting reaction mixture is concentrated, added water, and extracted with ethylacetate (3×100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a dark brown gummy material (0.900 g, 97% mass balance). The crude residue is purified by column chromatography over silica gel (230-400 mesh), eluting with 50% ethylacetate in petroleum ether, to obtain the title compound as a light yellow solid (0.270 g, 30% yield). M.p. 114.8-116.2° C. LC-ESI-HRMS of [M+H]+ shows 380.1125 Da. Calc. 380.113447 Da, dev. −2.5 ppm.

1. additionare added under a nitrogen atmosphere
2. customto attain spontaneously room temperature
3. custom(1 h)
4. temperaturefinally refluxed for 6 h
5. customThe resulting reaction mixture
6. concentrationis concentrated
7. additionadded water
8. extractionextracted with ethylacetate (3×100 ml)
9. dry with materialThe combined organic layers are dried over MgSO4
10. filtrationfiltered
11. customevaporated
12. customto afford a dark brown gummy material (0.900 g, 97% mass balance)
13. customThe crude residue is purified by column chromatography over silica gel (230-400 mesh)
14. washeluting with 50% ethylacetate in petroleum ether