Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

HRID 749994

反応式

HRID 749994 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O.Cl>O1CCOCC1.O.[Cu]I>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=3)=[CH:18][CH:19]=2)=[CH:5][CH:4]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 673N,N-DimethylglycineHCID 71014-BromobiphenylHCID 90154-MethoxyphenolHCID 10796Cesium carbonate

生成物 1

HCID 2668644-(4-Methoxyphenoxy)biphenyl収率 132.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a solution of 4-methoxyphenol (3.99 g, 32.17 mmol) and 4-bromobiphenyl (5 g, 21.45 mmol) in anhydrous dioxane (40 mL) were added cesium carbonate (13.98 g, 42.9 mmol) and N,N-dimethylglycine.HCl (0.898 g, 6.4 mmol). The reaction mixture was flushed with nitrogen. Copper (I) iodide (0.408 g, 2.145 mmol) was added and the reaction mixture was stirred at 90° C. for 18 h under an atmosphere of nitrogen. The mixture was diluted with water (100 mL) and extracted with EtOAc (250 mL). Aqueous layer was re-extracted with EtOAc (150 mls). The organic layers were combined, dried over anhydrous Na2SO4, and concentrated to obtain the title product 7.84 g.

後処理

  1. customThe reaction mixture was flushed with nitrogen
  2. extractionextracted with EtOAc (250 mL)
  3. extractionAqueous layer was re-extracted with EtOAc (150 mls)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-911a70802ff449069dc709acb0634781
出典データセット
uspto-grants-2008_07
特許番号
US07402684B2

関連ノート

読み込み中…