N-bromobutanimide → 2-Bromo-5-bromomethylpyridine

HRID 2199259Notes

Reaction equation

HRID 2199259 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridineYield 20%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

In 15 ml of carbon tetrachloride, 500 mg (2.92 mmol) of 2-bromo-5-methylpyridine was dissolved. To this solution, 623 mg (3.50 mmol) of N-bromosuccinimide and 10 mg of benzoyl peroxide were added, followed by heating under reflux for 19 hours. After completion of the reaction, the reaction liquid was returned to room temperature, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1). Thus, 143 mg of 2-bromo-5-bromomethylpyridine was obtained (Percentage Yield: 20%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 19 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-e07423687f92410f9777601a19440958
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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