Perchloric Acid → Tert-butyl 2-bromo-2-phenylacetate

HRID 1631946Notes

Reaction equation

HRID 1631946 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[Na+]>C(OC(C)(C)C)(=O)C>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([O:5][C:6]([CH3:11])([CH3:7])[CH3:2])=[O:4]

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 97919Bromo(phenyl)acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 11000147Tert-butyl 2-bromo-2-phenylacetate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A mixture of 7.9 g (44.1 mmol) of bromo-phenylacetic acid in tert-butyl acetate (100 ml) was cooled in an ice/water bath. 0.5 ml of perchloric acid was added, and the reaction solution was stirred at room temperature overnight. The reaction solution was slowly added to a saturated aqueous sodium bicarbonate solution (200 ml), and the organic phase was separated off. The aqueous phase was extracted twice with 60 ml of ethyl acetate each time, the combined organic phases were washed with saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate, and the solvent was removed in vacuo. Yield: 8.41 g (84%) of colorless oil

Workup

  1. temperaturewas cooled in an ice/water bath
  2. customthe organic phase was separated off
  3. extractionThe aqueous phase was extracted twice with 60 ml of ethyl acetate each time
  4. washthe combined organic phases were washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-be87328024834e6b89169a4009a55998
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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