反应详情

To a stirred and ice-cooled solution of sodium methoxide (0.296 g, 5.4848 mmol) in methanol (25 ml), commercial 4-(trifluoromethoxy)phenylacetonitrile (0.809 g, 4.0222 mmol) and 1-azido-2-fluoro-4-trifluoromethyl-benzene (0.750 g, 3.6565 mmol) are added portion wise. The reaction mixture is allowed to reach room temperature spontaneously overnight, concentrated in vacuo, added water, and extracted with ethylacetate (3×80 ml). The combined organic layers are dried over MgSO4, filtered and evaporated, to afford a brown solid residue (1.385 g, 94% mass balance). This crude material is purified by column chromatography over silica gel (230-400 mesh) eluting with 9% ethylacetate in petroleum ether, to obtain the title compound as an off-white solid (0.490 g, 33% yield). M.p. 134.2-134.9° C. LC-ESI-HRMS of [M+H]+ shows 407.0747 Da. Calc. 407.074282 Da, dev. 1 ppm.

1. additionare added portion wise
2. concentrationconcentrated in vacuo
3. additionadded water
4. extractionextracted with ethylacetate (3×80 ml)
5. dry with materialThe combined organic layers are dried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customto afford a brown solid residue (1.385 g, 94% mass balance)
9. customThis crude material is purified by column chromatography over silica gel (230-400 mesh)
10. washeluting with 9% ethylacetate in petroleum ether