Carbon Tetrachloride → 2-Bromo-5-bromomethylpyridine

HRID 1644002Notes

Reaction equation

HRID 1644002 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-bromomethylpyridineYield 105.4%

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) in carbon tetrachloride (40 mL, 400 mmol) was added benzoyl peroxide (230 mg, 950 μmol) and NBS (3.4 g, 19.2 mmol). The resulting mixture was heated at reflux overnight. The mixture was cooled at 0° C. and the NBS was removed by filtration. The filtrate was concentrated to yield 2-bromo-5-bromomethylpyridine (4.6 g), which was used directly in the next step.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux overnight
  3. customthe NBS was removed by filtration
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-46e10c9235364468909acbafc27f91bd
Source dataset
uspto-grants-2012_02
Patent number
US08119634B2

Reaction notes

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