Cesium carbonate → HCID 15941216, compound

HRID 500324Notes

Reaction equation

HRID 500324 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:10][CH:9]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 73784IodocyclopentaneHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol

Product 1

HCID 15941216HCID 15941216, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 40.0 g 4-(5-bromo-2-chloro-benzyl)-phenol and 71.0 g cesium carbonate in 300 mL ethanol are added 23 mL iodocyclopentane. The mixture is stirred at 60° C. over night and then cooled to ambient temperature. The ethanol is evaporated, and water is added to the residue. The resulting mixture is extracted with ethyl acetate, the combined extracts are dried over sodium sulfate, and the solvent is removed. The residue is filtered through silica gel (cyclohexane/ethyl acetate 100:1→10:1).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe ethanol is evaporated
  3. additionwater is added to the residue
  4. extractionThe resulting mixture is extracted with ethyl acetate
  5. dry with materialthe combined extracts are dried over sodium sulfate
  6. customthe solvent is removed
  7. filtrationThe residue is filtered through silica gel (cyclohexane/ethyl acetate 100:1→10:1)

Sources & evidence

ORD record
ord-6fe3618daa344dcd9e47e265f40e7163
Source dataset
uspto-grants-2010_08
Patent number
US07772191B2

Reaction notes

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