Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

HRID 749994

반응식

HRID 749994 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

HCID 2668644-(4-Methoxyphenoxy)biphenyl수율 132.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-911a70802ff449069dc709acb0634781
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402684B2

연결된 노트

불러오는 중…