Potassium Carbonate → 5-Nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine

HRID 450085Notes

Reaction equation

HRID 450085 reaction equation
[F:1][CH:2]([F:8])[C:3]([F:7])([F:6])[CH2:4]I.[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[N:16][CH:17]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:4][C:3]([F:7])([F:6])[CH:2]([F:8])[F:1])=[N:16][CH:17]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5428611,1,2,2-Tetrafluoro-3-iodopropaneHCID 178526703HCID 178526703, compound

Product 1

HCID 866211495-Nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridineYield 77.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1,2,2-Tetrafluoro-3-iodo propane (0.5 g, 2 mmol) was added to a mixture of 5-nitro-2-hydroxy pyridine (860 mg, 6.1 mmol) and potassium carbonate (1.4 g, 10 mmol) in DMF (10 ml) and the reaction heated at reflux for 6 hr. The reaction mixture was cooled to room temperature and filtered. The filtrate was diluted with ethyl acetate (50 ml), washed successively with bicarbonate solution, water, brine, and dried. Concentration to dryness yielded 5-nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine (394 mg, 75%) as an oil.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 6 hr
  3. filtrationfiltered
  4. additionThe filtrate was diluted with ethyl acetate (50 ml)
  5. washwashed successively with bicarbonate solution, water, brine
  6. customdried
  7. concentrationConcentration to dryness

Sources & evidence

ORD record
ord-1b8f09e14d914b8a81c0bd7976f8bc58
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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