Reaktion #42360

Reaktionsgleichung

3-cyanophenylboronic acid

2-bromopropene

sodium carbonate

→

title compound

3-Isopropenylbenzonitrile

Lösungsmittel

DME

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is degassed for 20 min with nitrogen
2. 2
   Sonstigethe reaction mixture degassed for 10 min
3. 3
   Temperaturheated
4. 4
   Temperaturat reflux overnight
5. 5
   Sonstigepartitioned between hexanes and water
6. 6
   ExtraktionThe aqueous layer is extracted with hexanes (3×75 mL)
7. 7
   WaschenThe combined organic layers are washed with brine
8. 8
   Trocknendried (magnesium sulfate)
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigePurification by flash column chromatography (9:1 hexanes/ethyl acetate)

Vorschrift

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).

Quelle