Iodine → 2-Fluoro-3-iodo-5-methylpyridine

HRID 1348892Notes

Reaction equation

HRID 1348892 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1.[I:14]I>C1COCC1>[F:6][C:7]1[C:12]([I:14])=[CH:11][C:10]([CH3:13])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 807IodineHCID 27746352-Fluoro-5-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 102432202-Fluoro-3-iodo-5-methylpyridineYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dilsopropylamine (7.0 mL, 50.0 mmol) in THF (100 mL) at −78° C. was treated with 2.5M n-butyllithium in hexanes (20 mL, 50.0 mmol), stirred for 15 minutes, treated dropwise with a solution of 2-fluoro-5-methylpyridine (5.55 g, 50.0 mmol) in THF (20.0 mL), stirred for 4 hours, treated slowly with a solution of iodine (12.7 g. 50.0 mmol) in THF (50 mL), quenched with water, and extracted with diethyl ether. The combined extracts were washed sequentially with Na2S2O3, water, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether to provide 7.24 g (61%) of 2-fluoro-3-iodo-5-methylpyridine.

Workup

  1. stirringstirred for 4 hours
  2. customquenched with water
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed sequentially with Na2S2O3, water, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with 6:1 hexanes/diethyl ether

Sources & evidence

ORD record
ord-0c8be9a0ec1b47508fc7ca9682cdd067
Source dataset
uspto-grants-2007_05
Patent number
US07211595B2

Reaction notes

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