Potassium Carbonate → HCID 178476544, compound

HRID 1191574Notes

Reaction equation

HRID 1191574 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[C:9]([O-:12])(=[O:11])[CH3:10].C([O-])(=O)C.[Pb+4:17].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:21][C:20]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[C:9]([O-:12])(=[O:11])[CH3:10].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:21][C:20]=1[Pb+3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59445929HCID 59445929, compoundHCID 178418268HCID 178418268, compound

Product 1

HCID 178476544HCID 178476544, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (3.76 g, 8.49 mmol) and mercuric diacetate (0.27 g, 0.85 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (25 ml). This mixture is warmed to 40° C., and 4-bromo-4′-chlorobiphenyl-3-yl-boronic acid (2.40 g, 7.72 mmol) is added in one portion, and the mixture is stirred and heated at this temperature for 4 hours. After cooling to room temperature, the mixture is diluted with chloroform (25 ml), cooled in an ice-bath, and powdered anhydrous potassium carbonate (2.75 g) is added rapidly, followed by rapid stirring for 5 minutes. The solids are removed by filtration, and the filtrate is concentrated to approximately a quarter of its volume. Hexane is added to induce crystallisation, and the solvents evaporated in vacuo. Trituration with hexane gives 4-bromo-4′-chlorobiphenyl-3-yllead triacetate (3.25 g), used without further purification in the next step.

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (25 ml)
  3. temperatureheated at this temperature for 4 hours
  4. temperatureAfter cooling to room temperature
  5. temperaturecooled in an ice-bath
  6. additionis added rapidly
  7. stirringby rapid stirring for 5 minutes
  8. customThe solids are removed by filtration
  9. concentrationthe filtrate is concentrated to approximately a quarter of its volume
  10. additionHexane is added
  11. customcrystallisation
  12. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-06f5a0b6eeaf46f9b4d0623fcb24ff53
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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