Carbon Tetrachloride → 2-Bromo-5-bromomethylpyridine

HRID 1182751Notes

Reaction equation

HRID 1182751 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.C(Cl)(Cl)(Cl)Cl.C1C(=O)N([Br:21])C(=O)C1>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:21])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 67184N-bromobutanimideHCID 5642162-Bromo-5-methylpyridine

Product 1

HCID 64246602-Bromo-5-bromomethylpyridine

Reagents, catalysts & solvents 1

HCID 7187Benzoyl PeroxideCatalyst

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromo-5-methylpyridine ((3.1 g, 17.4 mmol, 1 eq.) in carbon tetrachloride (40 mL, 400 mmol) was added benzoyl peroxide (230 mg, 950 μmol) and NBS (3.4 g, 19.2 mmol, 1.1 eq.). The resulting mixture was heated at reflux overnight. The mixture was cooled at 0° C. and filtered. The filtrate was concentrated to yield 2-bromo-5-bromomethylpyridine (4.6 g), which was used without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c0e31e2ebdb7409c98ad5b3ace99160a
Source dataset
uspto-grants-2014_03
Patent number
US08664227B2

Reaction notes

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