Bromine → Methyl 6-bromo-5-oxohexanoate

HRID 1057504Notes

Reaction equation

HRID 1057504 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10]C)=[O:8])(=[O:3])[CH3:2].[Br:12]Br>CO>[Br:12][CH2:2][C:1](=[O:3])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 24408BromineHCID 84130Ethyl 5-oxohexanoate

Product 1

HCID 582216Methyl 6-bromo-5-oxohexanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 4-acetylbutyrate was dissolved in MeOH (0.5M) and cooled to 0° C. Bromine (1.0 eq) was added dropwise and the mixture was stirred at room temperature for 18 hrs. The solvent was removed in vacuo and the residue was dissolved in ether, washed with water, saturated sodium bicarbonate, brine, dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatograpy (7% EtOAc/Hexanes). EI-MS m/z 224 (M+H)+.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ether
  3. washwashed with water, saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatograpy (7% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6f5fcd12af6c4ed4877937219857f1b5
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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