反应详情

温度

85 °C

3,5-dibromo-2-pyridinecarbonitrile (4.52g, 15.34 mmol) was dissolved in tetrahydrofuran (75 mL) and palladium tetrakis(triphenylphosphine) (0.887g, 0.767 mmol) and 4-fluorobenyl zinc chloride (46.02 mL, 0.5 M in tetrahydrofuran) were added. The mixture was heated at 85° C. for 1 hour. An additional 12.3 mL of 4-fluorobenyl zinc chloride was added and the reaction was heated 40 minutes and allowed to cool to ambient temperature. The mixture was diluted with water and ethyl acetate and several drops of 1 N hydrochloric acid were added and the reaction was extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel chromatography (0-100% ethyl acetate/hexanes gradient elution) gave 3-bromo-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (2.54g, 57% yield) as a pale yellow solid. 1H NMR (CDCl3) δ 8.48 (s, 1 H), 7.74 (s, 1 H), 7.15-7.11 (m, 2 H), 7.07-7.02 (m, 2 H), 4.02 (s, 2 H); MS m/z 292 (M+1).

1. temperaturethe reaction was heated 40 minutes
2. temperatureto cool to ambient temperature
3. additionwere added
4. extractionthe reaction was extracted with ethyl acetate
5. washThe organics were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customPurification
9. washby silica gel chromatography (0-100% ethyl acetate/hexanes gradient elution)