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

HRID 1631942Notes

Reaction equation

HRID 1631942 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-29049e44ea0d419cafd00e2db3c0a568
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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