Azobisisobutyronitrile → 3-Bromo-5-(dibromomethyl)-2-methoxypyridine

HRID 554650Notes

Reaction equation

HRID 554650 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH3:11])=[N:4][CH:5]=[C:6]([CH2:8][Br:9])[CH:7]=1.[Br:12]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:10][CH3:11])=[N:4][CH:5]=[C:6]([CH:8]([Br:12])[Br:9])[CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 585395103-Bromo-5-bromomethyl-2-methoxy-pyridine

Product 1

HCID 585396733-Bromo-5-(dibromomethyl)-2-methoxypyridine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromo-5-bromomethyl-2-methoxy-pyridine (6.03 g, 21.5 mmol), N-bromosuccinimide (4.09 g, 23.0 mmol), and azobisisobutyronitrile (one scoop) were combined in benzene (40 mL) and stirred at 80° C. for 4 hours. After cooling, the mixture was diluted with H2O and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give 3-Bromo-5-dibromomethyl-2-methoxy-pyridine.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f8bc6f6d6664cdab0b03c3ab78eda13
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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