Hydrochloric Acid → 4-(4-Methoxyphenoxy)biphenyl

HRID 2103319Notes

Reaction equation

HRID 2103319 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].CN(C)CC(O)=O.Cl>O1CCOCC1.[Cu]I.CCOC(C)=O.O>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

9

Reactant 5

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

Product 1

HCID 2668644-(4-Methoxyphenoxy)biphenyl

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromobiphenyl (1.16 g, 5 mmol), 4-methoxyphenol (413 mg, 3.33 mmol), Cs2CO3 (2.17 g, 6.66 mmol) in anhydrous dioxane (10 mL) was purged with nitrogen for 10 min. Then copper (I) iodide (18 mg, .096 mmol) and N,N-dimethylglycine.HCl (41 mg, 0.29 mmol) were added. Reaction was stirred at 90° C. over night. Reaction mixture was cooled and poured over 1:1 mixture of EtOAc/water. Organic layer was separated, washed with water, brine, dried over anhydrous MgSO4 and concentrated to give the crude product. It was used in next step without purification (1.26 g, 91%).

Workup

  1. customwas purged with nitrogen for 10 min
  2. customReaction
  3. customReaction mixture
  4. temperaturewas cooled
  5. customOrganic layer was separated
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-49455cdf3db14f26a551dd54ca78ff20
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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