N-bromobutanimide → 5-Bromo-2-(bromomethyl)pyridine

HRID 1663602Notes

Reaction equation

HRID 1663602 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Br:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 12010205-Bromo-2-methylpyridine

Product 1

HCID 234380625-Bromo-2-(bromomethyl)pyridineYield 51%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-bromo-2-methylpyridine (5.0 g) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (6.2 g) and 2,2′-azobis(2-methylpropionitrile) (239 mg) and the mixture was stirred at 85° C. for 1 hour. After cooling, the reaction mixture was filtered to remove the insoluble materials and the filtrate was concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=100:0→92:8) to give 5-bromo-2-bromomethyl-pyridine (3.7 g, yield: 51%).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customto remove the insoluble materials
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=100:0→92:8)

Sources & evidence

ORD record
ord-27cc528673e94acda580d7216786c3b0
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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