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

HRID 1672233Notes

Reaction equation

HRID 1672233 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-2fa4b35d4dd045a5a28ade11601b9dcf
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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