Potassium Carbonate → 2-[(3-Fluoro-4-nitrophenoxy)methyl]pyridine

HRID 618680Notes

Reaction equation

HRID 618680 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 218478032-[(3-Fluoro-4-nitrophenoxy)methyl]pyridineYield 17.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-fluoro-4-nitrophenol (3.14 g), 2-pyridylmethyl chloride (3.28 g), potassium carbonate (5.52 g) and DMF (20 ml) was stirred at ambient temperature for 16 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with water, dried (MgSO4) and evaporated. The residue was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluent to give 3-fluoro-4-nitrophenyl 2-pyridylmethyl ether (0.86 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-04714a995e5d4a42bbb895b4b308027c
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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