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

HRID 1892223Notes

Reaction equation

HRID 1892223 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-1d34fd03ad034315b8eab9e6ef4d80af
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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