Azobisisobutyronitrile → 6-Bromomethyl-nicotinic acid methyl ester

HRID 11709

Reaction equation

HRID 11709 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[N:6][CH:5]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:24])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 127522376-Bromomethyl-nicotinic acid methyl esterYield 34.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-methyl-nicotinic acid methyl ester (0.54 g, 3.57 mmol) in carbon tetrachloride (10 mL) was added 2,2′-azobis(2-methyl-proprionitrile) (0.030 g, 0.18 mmol) and N-bromosuccinimide (0.703 g, 3.95 mmol). The solution was stirred at reflux for 12 hours, cooled and concentrated in vacuo. Flash chromatography on silica gel provided the title compound (0.28 g).

Workup

  1. temperatureat reflux for 12 hours
  2. temperaturecooled
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdca795980844515b4650cb5656d3a34
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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