反应详情

To a solution of (3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2,5-difluorophenyl)acetonitrile (1.22 g, 4.30 mmol) in DMF (10 mL) was added 2-bromoethyl methyl ether (485 μl, 5.16 mmol) and potassium fluoride (0.5 g, 8.6 mmol). The mixture was stirred at room temperature for 15 hrs. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted with ethyl acetate. The combined organic portion was washed with brine, dried over sodium sulfate, filtered and concentrated in-vacuo to afford an orange oil, which was purified by column chromatography. Eluting with 30% ethyl acetate in hexanes gave 690 mg, 3.04 mmol (71%) of (2,5-difluoro-3-{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile as a colorless oil. 1H NMR (CDCl3): 6.75-6.69 (m, 2H), 4.17-4.15 (m, 2H), 3.78-3.74 (m, 4H), 3.44 (s, 3H); MS (EI) for C11H11NO2F2: 228 (MH+).

1. customThe reaction mixture was partitioned between ethyl acetate and water
2. extractionThe aqueous portion was extracted with ethyl acetate
3. washThe combined organic portion was washed with brine
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in-vacuo
7. customto afford an orange oil, which
8. customwas purified by column chromatography
9. washEluting with 30% ethyl acetate in hexanes