Azobisisobutyronitrile → 3-Bromo-6-(bromomethyl)-2-chloropyridine

HRID 527104

Reaction equation

HRID 527104 reaction equation
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Br:10]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:9])=[N:4][C:5]([CH2:8][Br:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27344183-Bromo-2-chloro-6-methylpyridine

Product 1

HCID 579845103-Bromo-6-(bromomethyl)-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

In 21 mL of carbon tetrachloride, 3-bromo-2-chloro-6-methylpyridine (880 mg, 4.26 mmol) was dissolved, and N-bromosuccinimide (682 mg, 3.83 mmol) and AIBN (70 mg, 0.426 mmol) were added, followed by stirring at 90° C. for one hour. The resulting reaction solution was concentrated, and the residue thus obtained was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5), whereby 3-bromo-6-(bromomethyl)-2-chloropyridine was obtained as a crude purified product.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated
  3. customthe residue thus obtained
  4. customwas purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)

Sources & evidence

ORD record
ord-753727f860cb43a9b55d455bf339e35d
Source dataset
uspto-grants-2016_05
Patent number
US09346787B2

Linked notes

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