Water → 5-(Bromomethyl)-2-chloropyridine

HRID 37855

Reaction equation

HRID 37855 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-19f91466f0b74cba80a0973a69dea6d8
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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