Sodium Iodide → 3,5-Dibromo-2-iodopyridine

HRID 2388024Notes

Reaction equation

HRID 2388024 reaction equation
Br[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[I-:10].[Na+].C(#N)CC.Cl[Si](C)(C)C>[OH-].[Na+]>[I:10][C:2]1[C:7]([Br:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 7854PropionitrileHCID 6287982,3,5-Tribromopyridine

Product 1

HCID 269675523,5-Dibromo-2-iodopyridineYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
105 °C

Procedure

To a sealed tube was added 2,3,5-tribromopyridine (5.63 g, 17.83 mol), sodium iodide (8.02 g, 53.50 mol), propanenitrile (45 mL), and chlorotrimethylsilane (2.26 mL, 17.83 mol). The resulting mixture was allowed to stir for 50 min at 105° C. The mixture was allowed to cool to rt and 2M NaOH (50 mL) was added. The mixture was extracted with EtOAc (2×80 mL). The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-iodo-3,5-dibromopyridine (5.4 g, 83%) as a solid.

Workup

  1. temperatureto cool to rt
  2. extractionThe mixture was extracted with EtOAc (2×80 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-485060bd59624b7b9df8637bdcafb301
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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