Reaktion #9049

Reaktionsgleichung

N-hydroxyphthalimide

Et3N

α,α′-dibromo-o-xylene

→

title compound

Ausbeute 46.0%

2-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dione

Ausbeute 46.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe resultant brown precipitate was filtered
2. 2
   Waschenwashed with CH2Cl2
3. 3
   workup.ADDITIONThe filtrate was diluted with EtOAc (40 mL) and water (30 mL)
4. 4
   Waschenthe organic phase washed with brine (1×30 mL)
5. 5
   Trocknendried (Na2SO4)
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc)

Vorschrift

To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc (40 mL) and water (30 mL) and the organic phase washed with brine (1×30 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc) to give the title compound (581 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 4.99 (s, 2H), 5.37 (s, 2H), 7.27–7.40 (m, 2H), 7.41–7.45 (m, 2H), 7.73–7.76 (m, 2H), 7.81–7.84 (m, 2H).

Quelle