Sodium Iodide → Methyl 5-broMo-6-iodonicotinate

HRID 420720Notes

Reaction equation

HRID 420720 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[N:6][C:7]=1Cl.[I:13][Si](C)(C)C.[I-].[Na+]>C(#N)CC>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[N:6][C:7]=1[I:13]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 85247Trimethylsilyl iodideHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 58001714Methyl 5-broMo-6-iodonicotinateYield 88%

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Procedure

To a mixture of methyl 5-bromo-6-chloro-3-pyridinecarboxylate (1 g, 3.99 mmol) in propionitrile (30 ml) was added iodotrimethylsilane (0.689 ml, 3.99 mmol) and then sodium iodide (1.795 g, 11.98 mmol). The mixture was stirred at room temperature for 30 min. Solvent was evaporated and the obtained solid was dissolved in H2O. pH was adjusted to basic with 2M NaOH and DCM was added. The organic phase was extracted, dried over Na2SO4, filtered and concentrated to give 1.2 g (79%) of desired compound as a yellow solid.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe obtained solid was dissolved in H2O
  3. additionwas added
  4. extractionThe organic phase was extracted
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9edd61a4a7d84587a399b29ee3cfb2bd
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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