Reaction #487562

Reaction equation

potassium carbonate

lead tetraacetate

5-bromo-2-ethylphenylboronic acid

→

5-bromo-2-ethylphenyllead triacetate

Yield 67.2%

Conditions

Workup

1. 1
   Otherthoroughly flushed with nitrogen
2. 2
   workup.ADDITIONis added anhydrous chloroform (42 ml)
3. 3
   Temperaturethe suspension is heated at this temperature for 5 hours
4. 4
   Temperatureto cool to room temperature
5. 5
   Temperatureby further cooling to 0° C.
6. 6
   Filtrationfiltration
7. 7
   ConcentrationThe filtrate is concentrated to half its volume
8. 8
   workup.ADDITIONfollowed by the addition of hexanes
9. 9
   Otherprecipitation
10. 10
    Otherthe solvent decanted
11. 11
    Washthe solid washed with hexanes

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.

Source