N-bromobutanimide → 2-Bromo-5-bromomethylpyridine

HRID 2375310Notes

Reaction equation

HRID 2375310 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C1C(=O)N([Br:16])C(=O)C1>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:16])=[CH:4][N:3]=1

Participants

5

Reactant 2

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

Product 1

HCID 64246602-Bromo-5-bromomethylpyridineYield 115.4%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 2-bromo-5-methylpyridine (170 g, 0.95 mol) in CCl4 (2 L) was added NBS (193 g, 1.08 mol) and benzoylperoxide (15 g) and the mixture was refluxed for 6 h. The reaction mixture was cooled down to rt and the solid formed was filtered off. The filtrate was concentrated affording 275 g of crude 2-bromo-5-bromomethylpyridine which was used without further purification in the next step (mixture of mono-bromo and di-bromo). [TLC, Rf=0.7, pet. ether/ethylacetate 9:1].

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. customthe solid formed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-615632313ee2468ba54a45d69275e05a
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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