Triacetoxyperiodinane → methyl 2-(4-bromophenyl)-2-oxoacetate

HRID 216415Notes

Reaction equation

HRID 216415 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([OH:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:26][CH:25]=1>C(Cl)Cl>[Br:23][C:24]1[CH:25]=[CH:26][C:27]([C:30](=[O:35])[C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 14571696Methyl 4-bromo-alpha-hydroxybenzeneacetate

Product 1

HCID 11218741methyl 2-(4-bromophenyl)-2-oxoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (7.6 g, 17.96 mmol) was added to an ambient temperature solution of methyl (4-bromophenyl)(hydroxy)acetate (4 g, 16.33 mmol) in methylene chloride (100 mL). After stirring at ambient temperature for 2 h, the reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1) and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded methyl (4-bromophenyl)(oxo)acetate.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1)
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b223bbfd84e44d45b8de04d71737f815
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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