2-Chlorophenol → Ethyl 2-(2-chlorophenoxy)acetate

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).

1. temperatureThe reaction mixture was then heated
2. temperatureto reflux
3. filtrationthe reaction mixture was filtered
4. customto remove insolubles
5. concentrationThe filtrate was then concentrated under reduced pressure
6. customto 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)

ORD record

ord-5026b40714514b03bf4016e828417bd4

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098211B2