Toluene → Dibenzyl ether

HRID 510457Notes

Reaction equation

HRID 510457 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([O:4][CH2:1][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 1140TolueneHCID 10796Cesium carbonate

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of compound 7, the properly substituted benzyl alcohol (1.1 eq), palladium(II) acetate (0.02 eq), 2-dit-butylphosphino-3,4,5,6-tertamethyl-2′,4′,6′-triisopropyl-1,1′biphenyl (0.02 eq), cesium carbonate (1.5 eq) in degassed toluene (4 ml/mmol) was heated at 75° C. for 16 hrs. Conversion was checked by TLC analysis. The solution was cooled to room temperature, diluted with DCM, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give compound 9 in yields varying from 30-80%.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88162ad7cf564a61a753c9511fc7b767
Source dataset
uspto-grants-2015_08
Patent number
US09096612B2

Reaction notes

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