Reaktion #11412

Reaktionsgleichung

2-chlorophenol

potassium carbonate

ethyl bromoacetate

→

Ethyl 2-chlorophenoxyacetate

Ausbeute 95.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was then heated
2. 2
   Temperaturto reflux
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   Sonstigeto remove insolubles
5. 5
   EinengenThe filtrate was then concentrated under reduced pressure
6. 6
   Sonstigeto give 8 as highly viscous, light yellow oil (32.0 g, 95% yield, 95% pure by LCMS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.16 (m, 1H); 7.03 (m, 1H); 6.76 (m, 1H); 6.71 (m, 1H); 4.90 (s, 2H); 4.12 (q, 2H); 1.33 (t, 3H)

Vorschrift

To a stirred solution of 2-chlorophenol (6, 20.0 g, 156 mmol) in acetone (300 mL) under nitrogen at ambient temperature were added potassium carbonate (23.7 g, 171 mmol) and ethyl bromoacetate (7, 26.0 g, 156 mmol). The reaction mixture was then heated to reflux and stirred at this temperature under nitrogen for 7 hours. After cooling to ambient temperature, the reaction mixture was filtered to remove insolubles. The filtrate was then concentrated under reduced pressure to give 8 as highly viscous, light yellow oil (32.0 g, 95% yield, 95% pure by LCMS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.16 (m, 1H); 7.03 (m, 1H); 6.76 (m, 1H); 6.71 (m, 1H); 4.90 (s, 2H); 4.12 (q, 2H); 1.33 (t, 3H).

Quelle