Water → 3-Bromo-2-(bromomethyl)-6-fluoropyridine

HRID 1749090Notes

Reaction equation

HRID 1749090 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[N:4][C:5]([F:8])=[CH:6][CH:7]=1.[Br:10]N1C(=O)CCC1=O.O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[C:3]([CH2:9][Br:10])=[N:4][C:5]([F:8])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 177501493-Bromo-6-fluoro-2-methylpyridine

Product 1

HCID 726988773-Bromo-2-(bromomethyl)-6-fluoropyridineYield 100.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-bromo-6-fluoro-2-methyl-pyridine (1.9 g, 10.0 mmol, 1.0 equiv) in CCl4 (40 mL) was added N-bromo-succinimide (2.14 g, 12.0 mmol, 1.2 equiv) followed by 2,2′-azobis(2-methylpropionitrile) (0.16 g, 1.0 mmol, 0.1 equiv). The mixture was heated at reflux for 16 h, then left to stand at ambient temperature for 24 h. Water (100 mL) was added and the product was extracted with dichloromethane. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to afford 3-bromo-2-bromomethyl-6-fluoro-pyridine (2.7 g) which was used without further purification. 1H NMR (400 MHz, CDCl3): 7.94 (1H, m), 7.84 (1H, m), 4.62 (2H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. waitleft
  4. extractionthe product was extracted with dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a781a0dd1db145d5a9cc5a134aafe812
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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