(5-Chloro-2-methylphenyl)boronic acid → [Diacetyloxy-(5-chloro-2-methylphenyl)plumbyl] acetate

HRID 72256

Reaction equation

HRID 72256 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:20]=[CH:21][C:22]([CH3:28])=[C:23](B(O)O)[CH:24]=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:20]=[CH:21][C:22]([CH3:28])=[C:23]([Pb+3:17])[CH:24]=1

Participants

3

Reactant 2

HCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476526[Diacetyloxy-(5-chloro-2-methylphenyl)plumbyl] acetateYield 99.8%

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (2.15 g, 4.85 mmol) and mercuric diacetate (0.15 g, 0.47 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (6 ml). This mixture is warmed to 40° C., and 5-chloro-2-methylphenylboronic acid (0.76 g, 4.46 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 5-chloro-2-methylphenyllead triacetate (2.27 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. customthen triturated with hexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f409628f8ca04feda77bcdf7b29091e2
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Linked notes

Loading…