Reaktion #9417

Reaktionsgleichung

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one

3-chlorophenylboronic acid

potassium carbonate

→

subtitled compound

Ausbeute 25.0%

5-(3-Chloro-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

Ausbeute 25.0%

Lösungsmittel

dimethoxyethane

ammonium chloride

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated
2. 2
   Temperaturto reflux for 2 hours
3. 3
   Extraktionextracted with EtOAc (×3)
4. 4
   TrocknenThe combined organic layers were dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by column chromatography (SiO2, EtOAc:hexane, 1:3)

Vorschrift

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.98 g, 4.07 mol) and tetrakis(triphenylphosphine)palladium(0) (0.239 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (35 cm3). After 15 min., 3-chlorophenylboronic acid (1.27 g, 8.13 mol) was added, followed by potassium carbonate (3.40 g, 45 mmol) in water (15 cm3). The reaction was heated to reflux for 2 hours and then stirred at room temperature overnight. The mixture was diluted with sat. ammonium chloride and extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane, 1:3) to afford the subtitled compound (0.284 g, 25%): mp 188–189° C.; 1H NMR (DMSO-d6) δ 3.34 (s, 6 H), 6.93 (d, 1 H, J=8.04 Hz), 7.38–7.35 (m, 1 H), 7.53–7.43 (m, 2 H), 7.61 (d, 1 H, J=7.68 Hz), 7.70 (s, 2 H), 10.40 (s, 1 H); IR (KBr) 3420, 3150, 3050, 1700 cm−1; MS (EI) m/z 270 (M−H)−; CHN calculated for C16H14ClNO+0.1 C4H8O2: C, 70.21; H, 5.32; N, 4.99. Found: C, 70.3; H, 5.44; N, 4.93.

Quelle