Water → 5-(Bromomethyl)-2-chloropyridine

HRID 1910803Notes

Reaction equation

HRID 1910803 reaction equation
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][N:29]=1.O>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:34][C:31]1[CH:32]=[CH:33][C:28]([Cl:27])=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5813932-Chloro-5-methyl-pyridine

Product 1

HCID 64246615-(Bromomethyl)-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-bromosuccinimide (6.1 g, 3.44 mmol) and benzoyl peroxide (218 mg, 0.09 mmol) were added successively to a solution of 2-chloro-5-methyl-pyridine (4.0 g, 3.13 mmol) in carbon tetrachloride (20 mL) and refluxed for 90 min. The reaction mixture was cooled to room temperature, water added and the organic layer separated. The organic layer was washed successively with water, brine, dried over anhydrous sodium sulfate and filtered. The resultant solution of 5-bromomethyl-2-chloro-pyridine was used as such for the next step.

Workup

  1. temperaturerefluxed for 90 min
  2. customthe organic layer separated
  3. washThe organic layer was washed successively with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-63c12345c93244ef932fe48c6c6dffda
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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