4-Bromo-2,6-diethylphenylboronic acid → [Diacetyloxy-(4-bromo-2,6-diethylphenyl)plumbyl] acetate
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]=1Participants
3
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).