Diethyl Ether → 4-ethyl-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole

Temperature

0 °C

To a suspension of copper(I) cyanide (0.037 g, 0.41 mmol) in anhydrous tetrahydrofuran (2 mL) at −78° C. under a nitrogen atmosphere was added a solution of methyllithium in diethyl ether (1.6 M, 0.54 mL, 0.86 mmol). The mixture was stirred at 0° C. until a clear, colorless solution formed, and then the solution was cooled back to −78° C. To the methylcuprate solution was added a solution of 4-(bromomethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl)-2H-1,2,3-triazole (i.e. the product of Example 6, Step A, 0.100 g, 0.21 mmol) in anhydrous tetrahydrofuran (4 mL). The mixture was stirred for 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (5 mL) and stirred vigorously at 23° C. until the solution turned deep blue in color. The reaction mixture was extracted with ethyl acetate (2×10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.038 g) as a clear, colorless oil.

1. customformed
2. temperaturethe solution was cooled back to −78° C
3. stirringThe mixture was stirred for 1 h
4. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (5 mL)
5. stirringstirred vigorously at 23° C. until the solution
6. extractionThe reaction mixture was extracted with ethyl acetate (2×10 mL)
7. dry with materialThe organic layer was dried (MgSO4)
8. concentrationconcentrated under reduced pressure
9. customto afford the crude product which
10. customwas purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes

ORD record

ord-1f4a5def69c54cfc9520dbebd1e2370d

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302999B2