Hexane → HCID 178476523, compound

HRID 341682Notes

Reaction equation

HRID 341682 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9](B(O)O)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.[C:18]([O-:21])(=[O:20])[CH3:19].[C:22]([O-:25])(=[O:24])[CH3:23].[C:26]([O-:29])(=[O:28])[CH3:27].C([O-])(=O)C.[Pb+4:34].CCCCCC.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:18]([O-:21])(=[O:20])[CH3:19].[C:22]([O-:25])(=[O:24])[CH3:23].[C:26]([O-:29])(=[O:28])[CH3:27].[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[CH:11]=[C:10]([CH3:12])[C:9]([Pb+3:34])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 594504934'-Chloro-3-methylbiphen-4-ylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476523HCID 178476523, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4′-Chloro-3-methylbiphen-4-ylboronic acid (6.0 g, 0.024 mol) is added in one portion to a mixture of lead tetraacetate (13.0 g, 0.029 mol) and mercuric acetate (0.38 g, 5 mol %) in chloroform (50 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 hours. 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 solid. Trituration with hexane (50 ml) affords a yellow solid which is dried under high vacuum. This solid is then dissolved in chloroform (100 ml), anhydrous potassium carbonate (42.5 g, 0.3 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-methylbiphen-4-yllead triacetate (7.8 g) as a cream solid.

Workup

  1. temperatureheated at 40° C. for 4 hours
  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 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-d86c44eba5194a95bd183c529860f9c3
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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