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Lead tetraacetate → HCID 178419342, compound

HRID 40478
Notes
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Reaction equation

HRID 40478 reaction equation
[CH3:1][C:2]([O-:4])=[O:3].[CH3:5][C:6]([O-:8])=[O:7].[CH3:9][C:10]([O-:12])=[O:11].CC([O-])=O.[Pb+2:17].[Br:18][C:19]1[CH:20]=[CH:21][C:22]([CH:28]2[CH2:30][CH2:29]2)=[C:23](B(O)O)[CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[C:2]([O-:4])(=[O:3])[CH3:1].[C:6]([O-:8])(=[O:7])[CH3:5].[C:10]([O-:12])(=[O:11])[CH3:9].[Br:18][C:19]1[CH:20]=[CH:21][C:22]([CH:28]2[CH2:30][CH2:29]2)=[C:23]([Pb+3:17])[CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11025Lead tetraacetateHCID 11430Potassium CarbonateHCID 58061455(5-Bromo-2-cyclopropylphenyl)boronic acid

Product 1

HCID 178419342HCID 178419342, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalyst
HCID 6212
Chloroform
Solvent

Procedure

To a solution of lead(IV)acetate (4.0 g, 0.0089 mol) and mercury(II)acetate (139 mg, 0.45 mmol) in chloroform (12 ml) at 50° C. is added 5-bromo-2-cyclopropylphenyl boronic acid (2.0 g, 0.0083 mol), and the solution is heated at this temperature for 5 hours. After cooling to room temperature the suspension is further cooled to 0° C. and anhydrous potassium carbonate (1.8 g) is added with rapid stirring for 2 minutes. The reaction mixture is then filtered (washing with additional chloroform), and the filtrate is concentrated to half its original volume and the crude product is precipitated with hexanes. Further concentration then filtration affords 5-bromo-2-cyclopropylphenyl lead triacetate as a beige solid.

Workup

  1. temperaturethe solution is heated at this temperature for 5 hours
  2. temperatureis further cooled to 0° C.
  3. filtrationThe reaction mixture is then filtered
  4. wash(washing with additional chloroform)
  5. concentrationthe filtrate is concentrated to half its original volume
  6. customthe crude product is precipitated with hexanes
  7. concentrationFurther concentration
  8. filtrationfiltration

Sources & evidence

ORD record
ord-7a0a3d5313034f89b09bb452f512b217
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530388B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes