Potassium Carbonate → [Diacetyloxy-(5-bromo-2-chlorophenyl)plumbyl] acetate

HRID 72272Notes

Reaction equation

HRID 72272 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:20]=[CH:21][C:22]([Cl:28])=[C:23](B(O)O)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>>[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:20]=[CH:21][C:22]([Cl:28])=[C:23]([Pb+3:17])[CH:24]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 467368165-Bromo-2-chlorophenylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476543[Diacetyloxy-(5-bromo-2-chlorophenyl)plumbyl] acetateYield 91.8%

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (26.83 g, 61 mmol) and mercuric diacetate (0.77 g, 2.4 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (50 ml) and the reaction mixture is stirred and heated to 40° C. 5-Bromo-2-chlorophenylboronic acid (11.39 g, 48 mmol) is added in one portion, and the reaction mixture is stirred at 40° C. for 4 hours. After cooling to room temperature potassium carbonate (3.34 g) is added, the mixture stirred vigorously for 5 minutes and then filtered. The filtrate is concentrated in vacuo to give 5-bromo-2-chlorophenyllead triacetate (25.33 g), used without further purification in the next step.

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (50 ml)
  3. stirringthe reaction mixture is stirred at 40° C. for 4 hours
  4. additionis added
  5. stirringthe mixture stirred vigorously for 5 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-5918d1ad95c54bb393b00a1f81bdb61d
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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