Azobisisobutyronitrile → Ethyl 2-bromo-2-(pyridin-3-yl)propanoate

HRID 46099Notes

Reaction equation

HRID 46099 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:2]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10726035Ethyl 2-pyridin-3-ylpropanoate

Product 1

HCID 58929638Ethyl 2-bromo-2-(pyridin-3-yl)propanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred mixture of ethyl 2-(pyridin-3-yl)propanoate (4.2 g, 23 mmol), CCl4 (100 mL), and N-bromosuccinimide (Aldrich, 4.6 g, 26 mmol) was added 2,2′-azobisisobutyronitrile (Aldrich, 0.8 g, 5 mmol) under N2 at room temperature. The mixture was gradually heated to reflux. After 7 h, the reaction mixture was concentrated in vacuo. The crude was purified by silica gel chromatography. Mass Spec. m/z+ion 258, 260 (M+1).

Workup

  1. temperatureThe mixture was gradually heated to reflux
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4f577d966df748f0a13b5935bf5eb8e4
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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