Potassium Carbonate → [Diacetyloxy-(4-bromo-2,6-dimethylphenyl)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]([CH3:25])[C:22](B(O)O)=[C:21]([CH3:29])[CH:20]=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:24]=[C:23]([CH3:25])[C:22]([Pb+3:17])=[C:21]([CH3:29])[CH:20]=1Participants
Conditions
- Temperature
- 40 °C
Procedure
To a mixture of lead tetraacetate (112.16 g, 0.25 mol) and mercuric diacetate (4.8 g, 0.015 mol), thoroughly flushed with nitrogen, is added anhydrous chloroform (480 ml). This mixture is warmed to 40° C. and 4-bromo-2,6-dimethylphenylboronic acid (48 g, 0.21 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, powdered anhydrous potassium carbonate (350 g) is added rapidly followed by rapid stirring for 5 minutes. The solids are removed by filtration 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-dimethylphenyl lead triacetate (30 g).
Workup
- customthoroughly flushed with nitrogen
- additionis added anhydrous chloroform (480 ml)
- temperatureheated at this temperature for 4 hours
- temperatureAfter cooling in an ice bath
- additionis added rapidly
- stirringby rapid stirring for 5 minutes
- customThe solids are removed by filtration
- concentrationthe filtrate is concentrated to approximately a quarter of its volume
- additionHexane is added
- customcrystallization
- customthe solvents evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-eba164fd293f4aa8ba386b74e293bed2
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895761B2
Reaction notes
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