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

HRID 2096596Notes

Reaction equation

HRID 2096596 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O-:11])=[O:10].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O.Cl>O1CCOCC1.[Cu]Cl.CCOC(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]([OH:11])=[O:10])=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 6931493HCID 6931493, compound

Product 1

HCID 122458712-(2-(4-Chlorophenoxy)phenyl)acetic acidYield 70%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-eb86cb56c50a4ff3bfef882c1c9b3de1
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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