Azobisisobutyronitrile → 3-Bromo-5-bromomethyl-2-methoxy-pyridine
Reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1.O>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][CH:5]=[C:6]([CH2:8][Br:11])[CH:7]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
3-Bromo-2-methoxy-5-methyl-pyridine (4.0 g, 19.8 mmol), N-bromosuccinimide (4.45 g, 23.8 mmol), and azobisisobutyronitrile (0.163 g, 0.99 mmol) were combined in benzene (40 mL) and stirred overnight at 80° C. The reaction was stirred for another 24 hours at 80° C., and then additional N-bromosuccinimide (1.8 g, 10.1 mmol), and azobisisobutyronitrile (catalytic) were added. After stirring for another 2 hours at 80° C., the mixture was diluted with H2O and extracted with CH2Cl2. The residue was purified by silica gel chromatography to give 3-bromo-5-bromomethyl-2-methoxy-pyridine.
Workup
- stirringThe reaction was stirred for another 24 hours at 80° C.
- stirringAfter stirring for another 2 hours at 80° C.
- extractionextracted with CH2Cl2
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-b498dc09ecbe4ac1b5fba8be030db570
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049015B2
Reaction notes
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