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

HRID 1924847Notes

Reaction equation

HRID 1924847 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-3bfdfc11e9e240edb48b595e62955d33
Source dataset
uspto-grants-2012_05
Patent number
US08178565B2

Reaction notes

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