Azobisisobutyronitrile → 6-(1-Bromoethyl)pyridine-3-carbonitrile

HRID 512507Notes

Reaction equation

HRID 512507 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH3:9])=[N:6][CH:7]=1.[Br:10]N1C(=O)CCC1=O.N(C(C)(C)[C:26]#[N:27])=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:10][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([C:26]#[N:27])=[CH:7][N:6]=1)[CH3:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 139797365-Bromo-2-ethylpyridine

Product 1

HCID 867115466-(1-Bromoethyl)pyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5-bromo-2-ethylpyridine (500 mg, 2.69 mmol), N-bromosuccinimide (484 mg, 2.69 mmol) and 2,2′-azo-bis(isobutyronitrile) (5 mg, 0.03 mmol) in chloroform is heated at reflux for 2 h. After stirring over night at room temperature, the reaction mixture is filtered, evaporated under reduced pressure and purified by preparative reversed-phase HPLC (Gilson, XBridge, gradient of acetonitrile in water, 0.1% HCOOH). Yield: 37 mg (5% of theory); Retention time HPLC: 0.89 min (Z011_S03).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationthe reaction mixture is filtered
  3. customevaporated under reduced pressure
  4. custompurified by preparative reversed-phase HPLC (Gilson, XBridge, gradient of acetonitrile in water, 0.1% HCOOH)
  5. custom0.89 min (Z011_S03)

Sources & evidence

ORD record
ord-629e19a122be462a824c0f93bccf22bb
Source dataset
uspto-grants-2015_08
Patent number
US09102624B2

Reaction notes

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