Hexane → HCID 178476532, compound

HRID 341695Notes

Reaction equation

HRID 341695 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9](B(O)O)=[C:8]([CH2:17][CH3:18])[CH:7]=2)=[CH:4][CH:3]=1.[C:21]([O-:24])(=[O:23])[CH3:22].[C:25]([O-:28])(=[O:27])[CH3:26].[C:29]([O-:32])(=[O:31])[CH3:30].C([O-])(=O)C.[Pb+4:37].CCCCCC.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:21]([O-:24])(=[O:23])[CH3:22].[C:25]([O-:28])(=[O:27])[CH3:26].[C:29]([O-:32])(=[O:31])[CH3:30].[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9]([Pb+3:37])=[C:8]([CH2:17][CH3:18])[CH:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 594505014'-Chloro-3,5-diethylbiphen-4-ylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476532HCID 178476532, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4′-Chloro-3,5-diethylbiphen-4-ylboronic acid (2.1 g, 0.007 mol) is added to a mixture of lead tetraacetate (3.67 g, 0.008 mol) and mercuric acetate (0.12 g, 5 mol %) in chloroform (15 ml) and the reaction mixture is stirred for 15 minutes at room temperature under an atmosphere of nitrogen, then stirred and heated at 40° C. for 4 hours. The reaction mixture is cooled to ambient temperature, filtered through a plug of diatomaceous earth and concentrated under reduced pressure to give an orange solid. Trituration with hexane (20 ml) affords a yellow solid which is dried under high vacuum. The solid is dissolved in chloroform (50 ml) and anhydrous potassium carbonate (11.6 g, 0.084 mol) is added. The suspension is stirred rapidly for 10 minutes, then filtered through plug of diatomaceous earth. The filtrate is concentrated under reduced pressure to give 4′-chloro-3,5-diethylbiphen-4-yllead triacetate (2.0 g) as a cream solid.

Workup

  1. stirringstirred
  2. temperatureheated at 40° C. for 4 hours
  3. temperatureThe reaction mixture is cooled to ambient temperature
  4. filtrationfiltered through a plug of diatomaceous earth
  5. concentrationconcentrated under reduced pressure
  6. customto give an orange solid
  7. customis dried under high vacuum
  8. dissolutionThe solid is dissolved in chloroform (50 ml)
  9. stirringThe suspension is stirred rapidly for 10 minutes
  10. filtrationfiltered through plug of diatomaceous earth
  11. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-32e63a74203444eda9fa2548e8363532
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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