3-Phenyloxolan-2-one → 4-Bromo-2-phenylbutanoic acid

HRID 1780213Notes

Reaction equation

HRID 1780213 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][O:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BrH:13].C(O)(=O)C>>[Br:13][CH2:11][CH2:12][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([OH:10])=[O:9]

Participants

3

Reactant 2

HCID 232693-Phenyloxolan-2-oneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 167406054-Bromo-2-phenylbutanoic acid

Procedure

The product of Example 3 (14.5 g, 90 mM) in 48% of HBr/acetic acid (100 ml) was left at room temperature overnight. The reaction was poured onto water (500 ml) and extracted with IPE 2x). The organic phase was washed with water, dried and evaporated to give the crystalline product (22 g) m.p. (cyclohexane).

Workup

  1. additionThe reaction was poured onto water (500 ml)
  2. extractionextracted with IPE 2x)
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-109c66fa61aa4645a24dbb2b0e25dd9e
Source dataset
uspto-grants-1997_05
Patent number
US05629432

Reaction notes

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