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

HRID 1643929Notes

Reaction equation

HRID 1643929 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-39e9528130bb45ab9eed687b5be9d320
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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