3,5-Dimethylbiphenyl-4-ylboronic acid → HCID 178476522, compound

HRID 43331Notes

Reaction equation

HRID 43331 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].[CH3:18][C:19]1[C:24](B(O)O)=[C:23]([CH3:28])[CH:22]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:20]=1>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].[CH3:18][C:19]1[C:24]([Pb+3:17])=[C:23]([CH3:28])[CH:22]=[C:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 594504813,5-Dimethylbiphenyl-4-ylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476522HCID 178476522, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of lead tetraacetate (4.3 g, 9.7 mmol) in dry chloroform (15 ml) at 40° C. is added 3,5-dimethylbiphen-4-ylboronic acid (2.0 g; 8.8 mmol) in one portion under an atmosphere of nitrogen. The mixture is stirred at 40° C. for 4 hours, and then is cooled to room temperature. The precipitate is removed by filtration, and the filtrate is then passed through a plug of potassium carbonate supported on diatomaceous earth to remove acetic acid. The filtrate is evaporated in vacuo to afford 3,5-dimethylbiphen-4-yllead triacetate (3.37 g) as a brown oil.

Workup

  1. temperatureis cooled to room temperature
  2. customThe precipitate is removed by filtration
  3. customto remove acetic acid
  4. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-81798756803946f894ec3e5cb0e77f4c
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Reaction notes

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