Azobisisobutyronitrile → 2-(4-(Bromomethyl)phenyl)pyridine

HRID 458510Notes

Reaction equation

HRID 458510 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][Br:14])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 782192-(p-Tolyl)pyridine

Product 1

HCID 98875912-(4-(Bromomethyl)phenyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-(2-Pyridyl)toluene, 2 mL (1.98 g, 11.7 mmol), N-bromosuccinimide (NBS), 2.5 g (14.0 mmol), and α,α′-azobis(isobutyronitrile) (AIBN), 23 mg (0.14 mmol) were suspended in 35 mL tetrachloromethane, and refluxed for 24 hours. The product was filtered, and the solvent removed from the filtrate by rotary evaporation. Equal amounts of chloroform and water were added and the product extracted. The chloroform layer was separated and dried, and the solvent removed. 4-(2-Pyridyl)benzyl bromide, 2 g, was obtained as a sticky yellow solid.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe product was filtered
  3. customthe solvent removed from the filtrate by rotary evaporation
  4. additionEqual amounts of chloroform and water were added
  5. extractionthe product extracted
  6. customThe chloroform layer was separated
  7. customdried
  8. customthe solvent removed

Sources & evidence

ORD record
ord-aebe37f25c0e45598e5623c14797471c
Source dataset
uspto-grants-2007_03
Patent number
US07192918B2

Reaction notes

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