Reaktion #561420

Reaktionsgleichung

4-methoxy benzyl bromide

2-chloro-5-nitrophenol

potassium carbonate

→

1-chloro-2-(4-methoxybenzyloxy)-4-nitrobenzene

Ausbeute 89.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationIt was then filtered
2. 2
   Waschenthe solid mass was washed with ethyl acetate (100 mL)
3. 3
   SonstigeThe solvent was removed under reduced pressure
4. 4
   Sonstigethe residue was purified by column chromatography (60-120 mesh silica gel)

Vorschrift

To a solution of 2-chloro-5-nitrophenol (10 g, 57.6 mmol) in acetonitrile (100 mL) was added potassium carbonate (11.7 g, 86 mmol) followed by 4-methoxy benzyl bromide (13.9 g, 69.1 mmol), at room temperature. The reaction mixture was stirred at room temperature for 18 h while monitoring by TLC. It was then filtered and the solid mass was washed with ethyl acetate (100 mL). The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica gel) using 2% MeOH in CHCl3 to give 1-chloro-2-(4-methoxybenzyloxy)-4-nitrobenzene (15 g, 89%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.85 (1H, s), 7.79 (1H, d, J=8.8 Hz), 7.53-7.51 (1H, d, J=8.4 Hz), 7.41-7.39 (2H, m), 6.95-6.87 (2H, m), 5.17 (2H, s), 3.82 (3H, s).

Quelle