Azobisisobutyronitrile → Methyl 2-bromo-2-(pyridin-2-yl)acetate

HRID 1025805Notes

Reaction equation

HRID 1025805 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 74264Methyl 2-pyridylacetate

Product 1

HCID 20540308Methyl 2-bromo-2-(pyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of methyl 2-pyridylacetate (10.0 g, 66.0 mmol), N-bromosuccinimide (13.0 g, 73.0 mmol) and 2,2′-azobisisobutyronitrile (0.50 g, 3.04 mmol) in carbon tetrachloride (120 mL) was irradiated with a sunlamp source for approximately 15 h. After filtration, the filtrate was concentrated in vacuo and the crude residue was purified by flash chromatography on silica gel (gradient elution; 5-10% EtOAc/hexane as eluent) to afford the title compound 5i.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe crude residue was purified by flash chromatography on silica gel (gradient elution; 5-10% EtOAc/hexane as eluent)

Sources & evidence

ORD record
ord-5d76323e805042a5b9609b8eecd38373
Source dataset
uspto-grants-2014_05
Patent number
US08729104B2

Reaction notes

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