Reacción #42360

Ecuación de reacción

3-cyanophenylboronic acid

2-bromopropene

sodium carbonate

→

title compound

3-Isopropenylbenzonitrile

Disolventes

DME

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixture is degassed for 20 min with nitrogen
2. 2
   Otrothe reaction mixture degassed for 10 min
3. 3
   Temperaturaheated
4. 4
   Temperaturaat reflux overnight
5. 5
   Otropartitioned between hexanes and water
6. 6
   ExtracciónThe aqueous layer is extracted with hexanes (3×75 mL)
7. 7
   LavadoThe combined organic layers are washed with brine
8. 8
   Secadodried (magnesium sulfate)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    OtroPurification by flash column chromatography (9:1 hexanes/ethyl acetate)

Procedimiento

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).

Fuente