5-(4-Chlorophenyl)-2-methylphenylboronic acid → HCID 178476525, compound

HRID 468215Notes

Reaction equation

HRID 468215 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].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27](B(O)O)[CH:26]=2)=[CH:21][CH:20]=1>>[C:1]([O-:4])(=[O:3])[CH3:2].[C:5]([O-:8])(=[O:7])[CH3:6].[C:9]([O-:12])(=[O:11])[CH3:10].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([Pb+3:17])[CH:26]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 594459235-(4-Chlorophenyl)-2-methylphenylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476525HCID 178476525, compoundYield 100%

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (2.44 g, 5.50 mmol) and mercuric diacetate (0.16 g, 0.50 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (6 ml). This mixture is warmed to 40° C., and 4′-chloro-4-methylbiphenyl-3-ylboronic acid (1.23 g, 5.00 mmol) is added in one portion, and the suspension is heated at this temperature for 5 hours. After cooling to room temperature the mixture is concentrated to a small volume, then triturated with hexanes and filtered to yield crude 4′-chloro-4-methylbiphenyl-3-yllead triacetate (2.93 g).

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (6 ml)
  3. temperaturethe suspension is heated at this temperature for 5 hours
  4. temperatureAfter cooling to room temperature the mixture
  5. concentrationis concentrated to a small volume
  6. customtriturated with hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-142e0719903240da81498c894a38bd23
Source dataset
uspto-grants-2014_01
Patent number
US08623907B2

Reaction notes

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