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

HRID 2096596ノート

反応式

HRID 2096596 の反応式
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

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 6931493HCID 6931493、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-eb86cb56c50a4ff3bfef882c1c9b3de1
出典データセット
uspto-grants-2013_05
特許番号
US08450308B2

反応ノート

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