Potassium Carbonate → HCID 178476531, compound

HRID 72292Notes

Reaction equation

HRID 72292 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9](B(O)O)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.[C:19]([O-:22])(=[O:21])[CH3:20].[C:23]([O-:26])(=[O:25])[CH3:24].[C:27]([O-:30])(=[O:29])[CH3:28].C([O-])(=O)C.[Pb+4:35].C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:19]([O-:22])(=[O:21])[CH3:20].[C:23]([O-:26])(=[O:25])[CH3:24].[C:27]([O-:30])(=[O:29])[CH3:28].[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH:11]=[C:10]([CH2:12][CH3:13])[C:9]([Pb+3:35])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 594504924'-Chloro-3-ethylbiphen-4-ylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476531HCID 178476531, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4′-Chloro-3-ethylbiphen-4-ylboronic acid (4.2 g, 0.016 mol) is added in one portion to a mixture of lead tetraacetate (7.86 g, 0.017 mol) and mercuric acetate (0.25 g, 5 mol %) in chloroform (23 ml) under an atmosphere of nitrogen. The reaction mixture is stirred at ambient temperature until dissolution is complete, and then heated at 40° C. for 4 hrs. The reaction mixture is cooled to ambient temperature, filtered through a plug of diatomaceous earth and the filtrate is concentrated under reduced pressure to give an orange colored solid. Trituration with hexanes (50 ml) affords a yellow solid which is dried under high vacuum. This solid is then dissolved in chloroform (100 ml), anhydrous potassium carbonate (26.7 g, 0.19 mol) is added and the suspension is stirred rapidly for 10 minutes. The mixture is filtered through a plug of diatomaceous earth, and the filtrate is concentrated under reduced pressure to give 4′-chloro-3-ethylbiphen-4-yllead triacetate (5.6 g) as a cream colored solid.

Workup

  1. temperatureheated at 40° C. for 4 hrs
  2. temperatureThe reaction mixture is cooled to ambient temperature
  3. filtrationfiltered through a plug of diatomaceous earth
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customto give an orange colored solid
  6. customis dried under high vacuum
  7. dissolutionThis solid is then dissolved in chloroform (100 ml)
  8. stirringthe suspension is stirred rapidly for 10 minutes
  9. filtrationThe mixture is filtered through a plug of diatomaceous earth
  10. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-46634a5b72094191a2b8075fbc404564
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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