Azobisisobutyronitrile → Ethyl 3-bromo-2-oxohexanoate

HRID 586370Notes

Reaction equation

HRID 586370 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH:5]([OH:10])[CH2:6][CH2:7][CH2:8][CH3:9])[CH3:2].[Br:12]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:11])[C:5](=[O:10])[CH:6]([Br:12])[CH2:7][CH2:8][CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 103589Hexanoic acid, 2-hydroxy-, ethyl ester

Product 1

HCID 22285486Ethyl 3-bromo-2-oxohexanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a modification of the method described in JCS Perkin Trans. I 1972, 2584, a mixture of 2-hydroxy-hexanoic acid ethyl ester (5 g, 31 mmol), N-bromosuccinimide (12 g, 67 mmol) and catalytic AIBN in anhydrous CCl4 (60 mL) is refluxed. After heating for about 20 minutes, the reaction initiates with evolution of a red-brown gas. After refluxing 4 hours, the resulting mixture is filtered and the filtrate evaporated at reduced pressure to obtain 3-bromo-2-oxo-hexanoic acid ethyl ester as a dark liquid. Step 2. Preparation of 3-(1-propyl)-imidazolo[1,2-a]pyridine-2-carboxylate

Workup

  1. temperatureis refluxed
  2. temperatureAfter heating for about 20 minutes
  3. temperatureAfter refluxing 4 hours
  4. filtrationthe resulting mixture is filtered
  5. customthe filtrate evaporated at reduced pressure

Sources & evidence

ORD record
ord-7ce332a3e6ee457f82a2a00d00f977ae
Source dataset
uspto-grants-2005_08
Patent number
US06936617B2

Reaction notes

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