Water → 4-Iodo-2-methoxypyridine

HRID 243757Notes

Reaction equation

HRID 243757 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][O-:10].[Na+].O>CO>[I:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:10][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70235702-Fluoro-4-iodopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 150197954-Iodo-2-methoxypyridineYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

500 ml of methanol was added to 59.4 g (253 mmol) of crude 2-fluoro-4-iodopyridine obtained in Step (b) so that it was dissolved in methanol, and 21.5 g (398 mmol) of sodium methoxide was added, followed by reflux with heating for 3 hours. 300 ml of water was added to terminate the reaction, and methanol was distilled off under reduced pressure. After extraction with ethyl ether, the organic layer was dried over sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure to obtain 56.7 g (crude yield: 91%) of crude 4-iodo-2-methoxypyridine.

Workup

  1. temperatureby reflux
  2. temperaturewith heating for 3 hours
  3. customto terminate
  4. customthe reaction, and methanol
  5. distillationwas distilled off under reduced pressure
  6. extractionAfter extraction with ethyl ether
  7. dry with materialthe organic layer was dried over sodium sulfate
  8. filtrationsubjected to filtration
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-404fbcb764e14f0da27eb9b8cd94239d
Source dataset
uspto-grants-2014_02
Patent number
US08653277B2

Reaction notes

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