Reaktion #339259

Reaktionsgleichung

potassium fluoride

tributyl tin hydride

4-bromo-5,7-Dimethoxy-2-(4-chloro-benzyl)-2,3-dihydro-isoindol

→

5,7-Dimethoxy-2-(4-chloro-benzyl)-2,3-dihydro-isoindol

Ausbeute 46.1%

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was refluxed in an oil bath for 2 h
2. 2
   FiltrationThe solids were filtered
3. 3
   Einengenthe filtrate was concentrated
4. 4
   SonstigeThe resulting material was purified

Vorschrift

To a solution of 4-bromo-5,7-Dimethoxy-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-lone (0.100 g, 0.25 mmol) in benzene under N2 atmosphere was added 2,2′-azobis(2-methyl proponitrile) AIBN (5.0 mg), followed by tributyl tin hydride (0.132 mL, 0.5 mmol). The resulting mixture was refluxed in an oil bath for 2 h. The reaction was monitored by GC-MS for the disappearance of starting material. The reaction mixture was cooled to room temperature and stirred with potassium fluoride (200 mg) for 45 min. The solids were filtered and the filtrate was concentrated. The resulting material was purified using column chromatography (typically 40% ethyl acetate in hexanes) to give 5,7-Dimethoxy-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-lone (0.035 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.82 (s, 3H), 3.95 (s, 3H), 4.15 (s, 2H), 4.69 (s, 2H), 6.43 (d, 2H), 7.25 (m, 4H). GC-MS: m/z 317 (M)+, 299 (M-18)+.

Quelle