Hydrogen Peroxide → (R)-2-(4-bromophenyl)propanoic acid

HRID 735697Notes

Reaction equation

HRID 735697 reaction equation
C([C@@H]1COC(=O)N1[C:14](=[O:24])[C@@H:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)[CH3:16])C1C=CC=CC=1.OO.[Li+].[OH-].[O-:29]S([O-])=O.[Na+].[Na+]>C1COCC1>[Br:23][C:20]1[CH:19]=[CH:18][C:17]([C@@H:15]([CH3:16])[C:14]([OH:24])=[O:29])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 54029560(R)-4-benzyl-3-((R)-2-(4-bromophenyl)propanoyl)oxazolidin-2-one

Product 1

HCID 12953949(R)-2-(4-bromophenyl)propanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 76B (209 mg, 0.54 mmol) in THF (5 mL) at 0° C., was added H2O2 (0.33 mL, 50%, 5.4 mmol) dropwise, followed by aq. LiOH (1.1 mL, 1.0 M, 1.1 mmol). The solution was stirred at rt for 2 h. Aq. Na2SO3 (1M, 20 mL) was added and stirred rt for 30 min. The aqueous phase was extracted with CH2Cl2 (2×10 mL), acidified to pH=2 with 1N HCl, and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated to give 76C (110 mg, 90%). MS (ESI) m/z 229.0 (M+H)+.

Workup

  1. stirringstirred rt for 30 min
  2. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7a567c7556184a0fba1f91e3071053d4
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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