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

HRID 2355769Notes

Reaction equation

HRID 2355769 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>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][Br:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 592970785-(Bromomethyl)-2-chloro-3-fluoropyridineYield 48%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 2-chloro-3-fluoro-5-methylpyridine (5.1 g, 35 mmol), N-bromosuccinimide (6.1 g, 35 mmol) and benzolyperoxide (0.16 g, 0.66 mmol) in carbon tetrachloride (100 mL) was refluxed overnight. Upon cooling down, the solid was filtered off and the filtrate was concentrated and loaded onto a silica gel column eluted with 5% EtOAc in hexane to give 3.77 g of the desired 2-chloro-3-fluoro-5-bromomethylpyridine as colorless oil in 48% yield. GC-MS calcd. for C6H4BrClFN: 224.46. Found: 224.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureUpon cooling down
  3. filtrationthe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. washeluted with 5% EtOAc in hexane

Sources & evidence

ORD record
ord-256d1e0ae02b41d1acb470ff38e094c7
Source dataset
uspto-grants-2010_07
Patent number
US07754888B2

Reaction notes

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