Water → 3-Fluoro-2-iodo-6-methylpyridine

HRID 878758Notes

Reaction equation

HRID 878758 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[I-:10].[Na+].CNCCNC.O>O1CCOCC1.[Cu]I>[F:8][C:7]1[C:2]([I:10])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 248203182-Bromo-3-fluoro-6-methylpyridine

Product 1

HCID 867073913-Fluoro-2-iodo-6-methylpyridineYield 94%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-bromo-3-fluoro-6-methylpyridine (1000 mg, 5.26 mmol) in 1,4-dioxane (16 mL) were added sodium iodide (1580 mg, 10.52 mmol), copper (I) iodide (150 mg, 0.26 mmol), N,N′-dimethylethylenediamine (62 μL, 0.58 mmol) under argon atmosphere. The reaction solution was heated to reflux for 4 hours, cooled to room temperature, and then to the reaction solution was added water. The mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with aqueous citric acid solution and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give 3-fluoro-2-iodo-6-methylpyridine (1169 mg, 94%) as a white powder.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 4 hours
  3. extractionThe mixture was extracted with ethyl acetate twice
  4. washwashed with aqueous citric acid solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69cf8ff0eaaa4393939385cc388c468b
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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