Hydrochloric Acid → 2-(2-(4-Chlorophenoxy)phenyl)acetic acid

Temperatur

50 °C

2-(2-Bromophenyl)acetate (10 g, 43.7 mmol) and 4-chlorophenol (5.61 g, 43.7 mmol) were dissolved in dioxane (150 mL) whiling warming to 50° C. To the resulting solution were added, under stirring in an inert nitrogen atmosphere, cesium carbonate (28.35 g, 87.4 mmol) and copper (I) chloride (1.73 g, 17.48 mmol). Finally N,N-dimethylglycine (0.9 g, 8.74 mmol) was added to the green suspension. The mixture was heated at 110° C. for 2 days while stirring. The mixture was filtrated over dicalite, which was washed with dioxane (20 mL). The dioxane was removed in vacuum to leave brownish oil. EtOAc was added to the oil and the pH of the resulting mixture was adjusted to 1 by addition of 1 M HCl. The organic phase was washed with saturated brine, dried over Na2SO4 and concentrated under vacuum to yield the crude product, which was purified by column chromatography to give 2-(2-(4-chlorophenoxy)phenyl)acetic acid (8 g, 70%).

1. additionTo the resulting solution were added
2. temperatureThe mixture was heated at 110° C. for 2 days
3. filtrationThe mixture was filtrated over dicalite, which
4. washwas washed with dioxane (20 mL)
5. customThe dioxane was removed in vacuum
6. customto leave brownish oil
7. washThe organic phase was washed with saturated brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under vacuum
10. customto yield the crude product, which
11. customwas purified by column chromatography

ORD-Eintrag

ord-eb86cb56c50a4ff3bfef882c1c9b3de1

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08450308B2