4-Bromo-2-ethylphenylboronic acid → HCID 178476529, compound

HRID 341698

Reaction equation

HRID 341698 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]=[CH:23][C:22](B(O)O)=[C:21]([CH2:28][CH3:29])[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]=[CH:23][C:22]([Pb+3:17])=[C:21]([CH2:28][CH3:29])[CH:20]=1

Participants

3

Reactant 2

HCID 592760174-Bromo-2-ethylphenylboronic acidHCID 178418268HCID 178418268, compound

Product 1

HCID 178476529HCID 178476529, compoundYield 44.8%

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (53 g, 0.12 mol) and mercuric diacetate (2.5 g, 0.0078 mol), thoroughly flushed with nitrogen, is added anhydrous chloroform (250 ml). This mixture is warmed to 40° C. and 4-bromo-2-ethylphenylboronic acid (25 g, 0.11 mol) is added in one portion and the mixture is stirred and heated at this temperature for 4 hours. After cooling to room temperature, cooled in an ice bath, 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-ethylphenyl lead triacetate (28 g).

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (250 ml)
  3. temperatureheated at this temperature for 4 hours
  4. temperatureAfter cooling to room temperature
  5. temperaturecooled in an ice bath
  6. filtrationfiltered through a plug of diatomaceous earth
  7. concentrationthe filtrate is concentrated to approximately a quarter of its volume
  8. additionHexane is added
  9. customcrystallization
  10. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-66c96b4989b54d7cac56c093b825e16e
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Linked notes

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