N-bromobutanimide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

HRID 623285

Reaction equation

HRID 623285 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH3:9])=[CH:4][N:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 135413652-Chloro-3-fluoro-5-methylpyridine

Product 1

HCID 592970785-(Bromomethyl)-2-chloro-3-fluoropyridineYield 51%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methyl pyridine was dissolved in 80 ml of carbon tetrachloride, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added thereto, and the resulting mixture was heated and refluxed overnight. After the reaction was completed, the reaction solution was returned to room temperature, concentrated under reduced pressure and purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to obtain 3.06 g (yield 51%) of 5-(bromomethyl)-2-chloro-3-fluoropyridine.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperaturerefluxed overnight
  3. customwas returned to room temperature
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-0de255f4db904a38a841d8ba9c0a04cb
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Linked notes

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