Hexane → HCID 178476523, compound

HRID 72297Notes

Reaction equation

HRID 72297 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 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 hexane (50 ml) to afford a yellow solid which was 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 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. customwas 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-871979ffe05b49378bd3f1888db9ceb0
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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