N-bromobutanimide → 5-Bromo-2-(1-bromoethyl)pyridine

HRID 850117Notes

Reaction equation

HRID 850117 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1)[CH3:2].[Br:10]N1C(=O)CCC1=O>ClCCCl>[Br:10][CH:1]([C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 139797365-Bromo-2-ethylpyridine

Product 1

HCID 226162815-Bromo-2-(1-bromoethyl)pyridineYield 80%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2-ethyl-5-bromopyridine (1.86 g, 10 mmol), N-bromosuccinimide (1.78 g, 10 mmol) in 1,2-dichloroethane (20 ml) was brought to reflux before the addition of azoisobutyronitrile (AIBN) (20 mg). The solution was then refluxed for a further two hours. The cooled suspension was filtered and evaporated in vacuo. Purification by column chromatography (silica gel, eluting with 1:1 dichloromethane/hexane) gave the desired product as a pale yellow oil (2.12 g, 80%).

Workup

  1. temperatureThe solution was then refluxed for a further two hours
  2. filtrationThe cooled suspension was filtered
  3. customevaporated in vacuo
  4. customPurification
  5. washby column chromatography (silica gel, eluting with 1:1 dichloromethane/hexane)

Sources & evidence

ORD record
ord-a273fbe0a5ce4e9ba3d01fa0568a7cf2
Source dataset
uspto-grants-2000_01
Patent number
US06015825

Reaction notes

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