Hydrogen Bromide → 3-Benzyl-4-bromo-butyric acid

HRID 8218Notes

Reaction equation

HRID 8218 reaction equation
[CH2:1]([CH:8]1[CH2:12][O:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:14]>C(O)(=O)C>[CH2:1]([CH:8]([CH2:12][Br:14])[CH2:9][C:10]([OH:11])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5150640Dihydro-4-(phenylmethyl)-2(3H)-furanone

Product 1

HCID 156918353-Benzyl-4-bromo-butyric acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-benzyl-dihydrofuran-2-one (1.0 g, 5.6 mmol), acetic acid (1.7 mL), HBr (33% in acetic acid, 2.0 mL) is heated at 80° C. for 4 h. The mixture is cooled to room temperature, poured into ice-water (20 mL), and extracted with chloroform (2×30 mL). The combined organic extracts are washed with water and brine, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo to yield 3-benzyl-4-bromo-butyric acid, 1.5 g (99%), as a colorless liquid.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with chloroform (2×30 mL)
  3. washThe combined organic extracts are washed with water and brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d9b0d77c42e4e83b987cc8dcbc78150
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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