Cesium carbonate → Diphenyl Ether

HRID 901733Notes

Reaction equation

HRID 901733 reaction equation
Cl[C:2]1[CH:30]=[CH:29][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10](N3C=C(C4C=CC=CC=4O)N=C3CC(C)C)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].S([O-])(=O)(=O)C>CN(C=O)C.O>[C:7]1([O:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:30][CH:29]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 85257MethanesulfonateHCID 66977442{1-[4-(4-Chloro-phenoxy)-phenyl]-2-isobutyl-1H-imidazol-4-yl}phenol

Product 1

HCID 7583Diphenyl Ether

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

{1-[4-(4-Chloro-phenoxy)-phenyl]-2-isobutyl-1H-imidazol-4-yl}phenol (2 mmol) was added to a solution of Cs2CO3 (10 eq., 20 mmol) in anhydrous DMF (5 ml). This was followed by addition of the mesylate obtained above and the reaction mixture was heated to 90° C. for 2–3 h. The reaction mixture was then cooled to rt, diluted with cold water and the product was extracted with DCM. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give desired phenyl ether.

Workup

  1. customobtained above and the reaction mixture
  2. temperatureThe reaction mixture was then cooled to rt
  3. extractionthe product was extracted with DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-469e85dd364949e99748d542ffdc91f8
Source dataset
uspto-grants-2008_04
Patent number
US07361678B2

Reaction notes

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