4-Bromo-2,6-diethylphenylboronic acid → [Diacetyloxy-(4-bromo-2,6-diethylphenyl)plumbyl] acetate

HRID 341701Notes

Reaction equation

HRID 341701 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]=[C:23]([CH2:25][CH3:26])[C:22](B(O)O)=[C:21]([CH2:30][CH3:31])[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].[Br:18][C:19]1[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([Pb+3:17])=[C:21]([CH2:30][CH3:31])[CH:20]=1

Participants

3

Reactant 2

HCID 595626634-Bromo-2,6-diethylphenylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476530[Diacetyloxy-(4-bromo-2,6-diethylphenyl)plumbyl] acetateYield 44.1%

Conditions

Temperature
60 °C

Procedure

To a mixture of lead tetraacetate (9.5 g, 0.02 mol) and mercuric diacetate (0.25 g, 0.78 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (25 ml) and toluene (25 ml). This mixture is warmed to 60° C. and 4-bromo-2,6-diethylphenylboronic acid (5 g, 0.019 mol) is added in one portion and the mixture is stirred and heated at this temperature for 4 hours. After cooling in an ice bath, the mixture is filtered through a plug of diatomaceous earth and the filtrate is concentrated to approximately a quarter of its volume. Hexane is added to induce crystallization and the solvents evaporated under reduced pressure. Trituration with hexane gives 4-bromo-2,6-diethylphenyllead triacetate (5 g).

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (25 ml) and toluene (25 ml)
  3. temperatureheated at this temperature for 4 hours
  4. temperatureAfter cooling in an ice bath
  5. filtrationthe mixture is filtered through a plug of diatomaceous earth
  6. concentrationthe filtrate is concentrated to approximately a quarter of its volume
  7. additionHexane is added
  8. customcrystallization
  9. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-a4b8152f0e064c1e8e46a22b3e50d7f1
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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