反应详情

To a stirred solution of 3-cyanophenylboronic acid (10.0 g, 68.05 mmol) dissolved in DME (340 mL) is added 2-bromopropene (6.86 g, 56.7 mmol), and sodium carbonate (62.3 mL of a 2 M solution in water, 124.7 mmol). The reaction mixture is degassed for 20 min with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (2.54 g, 2.2 mmol) is added, the reaction mixture degassed for 10 min, and heated at reflux overnight. The reaction mixture is cooled to room temperature and then partitioned between hexanes and water. The aqueous layer is extracted with hexanes (3×75 mL). The combined organic layers are washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (9:1 hexanes/ethyl acetate) provides the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.96 (m, 1H), 7.85 (d, J=8 Hz, 1H), 7.75 (d, J=8 Hz, 1H), 7.56 (m, 1H) 5.58 (s, 1H), 5.23 (m, 1H), 2.13 (s, 3H).

1. customThe reaction mixture is degassed for 20 min with nitrogen
2. customthe reaction mixture degassed for 10 min
3. temperatureheated
4. temperatureat reflux overnight
5. custompartitioned between hexanes and water
6. extractionThe aqueous layer is extracted with hexanes (3×75 mL)
7. washThe combined organic layers are washed with brine
8. dry with materialdried (magnesium sulfate)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customPurification by flash column chromatography (9:1 hexanes/ethyl acetate)