Reaktion #1483240

Reaktionsgleichung

potassium carbonate

benzyl bromide

3-Bromo-5-chloro-phenol

→

pale yellow oil

Ausbeute 90.0%

1-Benzyloxy-3-bromo-5-chloro-benzene

Ausbeute 90.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 2 h.
2. 2
   Filtrationfiltrated
3. 3
   Einengenthe filtrate was concentrated to dryness
4. 4
   SonstigeThe residue was chromatographed over a short column of silica
5. 5
   Wascheneluting with DCM/PA 1:4
6. 6
   Sonstigethe pink color of the product fractions (at the front) was removed with active carbon
7. 7
   FiltrationAfter filtration and evaporation

Vorschrift

2.54 g 3-Bromo-5-chloro-phenol was dissolved in 50 mL acetone. Subsequently were added 8.04 g potassium carbonate, 1.52 mL benzyl bromide and 0.86 g tetrabutylammonium iodide. The mixture was refluxed for 2 h., cooled to room temperature and filtrated, and the filtrate was concentrated to dryness. The residue was chromatographed over a short column of silica, eluting with DCM/PA 1:4, and the pink color of the product fractions (at the front) was removed with active carbon. After filtration and evaporation, 3.11 g (90%) of a pale yellow oil was obtained. 1H NMR (400 MHz, CDCl3) δ 5.03 (s, 2H), 6.92 (t, J=2 Hz, 1H), 7.03 (t, J=2 Hz, 1H), 7.12 (t, J=1.5 Hz, 1H), 7.31-7.45 (m, 5H).

Quelle