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

HRID 1408783노트

반응식

HRID 1408783 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

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. 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 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%).

후처리

  1. temperaturewarming to 50
  2. additionTo the resulting solution were added
  3. temperatureThe mixture was heated at 110 for 2 days
  4. filtrationThe mixture was filtrated over dicalite, which
  5. washwas washed with dioxane (20 mL)
  6. customThe dioxane was removed in vacuum
  7. customto leave brownish oil
  8. washThe organic phase was washed with saturated brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated under vacuum
  11. customto yield the crude product, which
  12. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-0f9a8755df104271914fa372e8996894
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921359B2

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