Perchloric Acid → tert-Butyl 2-bromo-3-phenylpropionate

HRID 1643925Notes

Reaction equation

HRID 1643925 reaction equation
[Br:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=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]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][C:7]([CH3:12])([CH3:8])[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 24247Perchloric AcidHCID 1675442-Bromo-3-phenylpropanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 12158486tert-Butyl 2-bromo-3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

A mixture of 10.1 g (44.1 mmol) of 2-bromo-3-phenylpropionic acid in tert-butyl acetate (150 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. The residue was purified by chromatography on silica gel (mobile phase gradient 20% acetic acid in cyclohexane). Yield: 6.76 g (54%) 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
  7. customThe residue was purified by chromatography on silica gel (mobile phase gradient 20% acetic acid in cyclohexane)

Sources & evidence

ORD record
ord-bf0e46c1a588438882ac8a57ddd34d89
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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