Acetic Acid → (3S)-3-acetyloxy-4-bromobutanoic acid

HRID 1356567

Reaction equation

HRID 1356567 reaction equation
[OH:1][C@@H:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.[BrH:8].[C:9]([OH:12])(=O)[CH3:10]>C(Cl)Cl>[C:9]([O:1][C@H:2]([CH2:7][Br:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:12])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 72693893-Hydroxybutyrolactone, (3S)-

Product 1

HCID 2733880(3S)-3-acetyloxy-4-bromobutanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a 2 l of three-necked flask equipped with reflux condenser, thermometer and mechanical stirrer were charged (S)-3-hydroxy-γ-butyrolactone (102 g) and 30% of hydrobromic acid in acetic acid (675 g, 2.5 eq.). The mixture was stirred at 40° C. for 3 hours. After cooling the reaction mixture, methylene chloride (1000 ml) was added to it. The reaction mixture was washed with aqueous solution of sodium acetate. The organic layer was separated, dried over magnesium sulfate, and concentrated to afford (S)-3-acetoxy-4-bromobutyric acid (213 g, 95%).

Workup

  1. customTo a 2 l of three-necked flask equipped
  2. temperaturewith reflux condenser
  3. additionwas added to it
  4. washThe reaction mixture was washed with aqueous solution of sodium acetate
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-811ace35f479451696a4894ed030bdba
Source dataset
uspto-grants-2003_07
Patent number
US06586616B1

Linked notes

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