Water → Methyl 2-bromo-3-cyclopropyl-3-oxopropanoate

HRID 389103

Reaction equation

HRID 389103 reaction equation
[CH:1]1([C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:3][CH2:2]1.Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[Br:22]N1C(=O)CCC1=O.O>C(OCC)(=O)C>[Br:22][CH:5]([C:4]([CH:1]1[CH2:3][CH2:2]1)=[O:10])[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 24840Magnesium perchlorateHCID 67184N-bromobutanimideHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 58243876Methyl 2-bromo-3-cyclopropyl-3-oxopropanoateYield 106.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-cyclopropyl-3-oxopropanoate (2.0 g) and magnesium perchlorate (940 mg) were dissolved in ethyl acetate (20 ml), followed by stirring at room temperature for 5 minutes, and N-bromosuccinimide (2.76 g) was added thereto, followed by stirring at room temperature for 4 hours. Water was added thereto, followed by extraction with ethyl acetate, the organic layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain, as a colorless oily product, methyl 2-bromo-3-cyclopropyl-3-oxopropanoate (3.32 g).

Workup

  1. stirringby stirring at room temperature for 4 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-867fd3f19a2344928aaca2959a94929d
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Linked notes

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