Potassium Carbonate → HCID 178476533, compound

HRID 72261Notes

Reaction equation

HRID 72261 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]([CH2:28][CH3:29])=[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]([CH2:28][CH3:29])=[C:23]([Pb+3:17])[CH:24]=1

Participants

4

Conditions

Temperature
40 °C

Procedure

To a mixture of lead tetraacetate (13.7 g, 31.00 mmol) and mercuric diacetate (0.47 g, 1.50 mmol), thoroughly flushed with nitrogen, is added anhydrous chloroform (42 ml). This mixture is warmed to 40° C., and 5-bromo-2-ethylphenylboronic acid (6.50 g, 28.00 mmol) is added in one portion and the suspension is heated at this temperature for 5 hours. The mixture is then allowed to cool to room temperature, followed by further cooling to 0° C. then addition of powdered anhydrous potassium carbonate (3.22 g) with rapid stirring for 5 minutes then filtration. The filtrate is concentrated to half its volume, followed by the addition of hexanes to induce precipitation. This mixture is further concentrated, the solvent decanted, and the solid washed with hexanes to afford 5-bromo-2-ethylphenyllead triacetate (10.69 g) as a sandy coloured solid.

Workup

  1. customthoroughly flushed with nitrogen
  2. additionis added anhydrous chloroform (42 ml)
  3. temperaturethe suspension is heated at this temperature for 5 hours
  4. temperatureto cool to room temperature
  5. temperatureby further cooling to 0° C.
  6. filtrationfiltration
  7. concentrationThe filtrate is concentrated to half its volume
  8. additionfollowed by the addition of hexanes
  9. customprecipitation
  10. customthe solvent decanted
  11. washthe solid washed with hexanes

Sources & evidence

ORD record
ord-d5ee4e3894d5426d8bef8c22c7b966bb
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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