Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

HRID 1909684Notes

Reaction equation

HRID 1909684 reaction equation
[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

Participants

9

Reactant 5

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

Product 1

HCID 2668644-(4-Methoxyphenoxy)biphenylYield 132.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4a2980addc0c4dd9ba79727735dc33a8
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

Loading…