Azobisisobutyronitrile → 6-(Bromomethyl)pyridine-3-carbonitrile

HRID 1471761Notes

Reaction equation

HRID 1471761 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[Br:10]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2819956-Methylpyridine-3-carbonitrile

Product 1

HCID 219277766-(Bromomethyl)pyridine-3-carbonitrileYield 37.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

Into a 250-mL round-bottom flask, was placed a solution of 6-methylpyridine-3-carbonitrile (8 g, 67.72 mmol, 1.00 equiv) in CCl4 (125 mL). N-Bromosuccinimide (13.4 g, 75.29 mmol, 1.10 equiv), and AIBN (480 mg, 2.92 mmol, 0.04 equiv) were added to the reaction solution. The resulting solution was stirred for 5 h at 85° C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5) as eluent to yield 5 g (37%) of 6-(bromomethyl)pyridine-3-carbonitrile as a beige solid.

Workup

  1. customInto a 250-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-bf24625a23ea48dbb7471a90ec8a2e6e
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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