Sodium hydride → HCID 86634744, compound

HRID 911010Notes

Reaction equation

HRID 911010 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[CH:16]=[C:15]([Cl:20])[N:14]=1>CN(C=O)C>[Cl:12][C:13]1[CH:18]=[C:17]([O:9][C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])[CH:16]=[C:15]([Cl:20])[N:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27665Pyridine, 2,4,6-trichloro-HCID 943922,6-Difluorophenol

Product 1

HCID 86634744HCID 86634744, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Difluorophenol (10.0 mmol) is added to a mixture of sodium hydride (240 mg, 10 mmol) in DMF (6 mL). The reaction mixture is stirred for 30 minutes at room temperature. The reaction mixture is cooled to 0° C., and 2,4,6-trichloropyridine is added. The reaction mixture is stirred at 0° C. for 1 hour, then at room temperature for 4 hours. The reaction mixture is partitioned between ethyl acetate and water, the organic layer is washed with 2N NaOH, water, brine, dried, and concentrated. The residue is purified via chromatography eluting with 5:1 hexane:ethyl acetate to afford 2,6-dichloro-4-(2,6-difluorophenoxy)pyridine.

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. stirringThe reaction mixture is stirred at 0° C. for 1 hour
  3. waitat room temperature for 4 hours
  4. customThe reaction mixture is partitioned between ethyl acetate and water
  5. washthe organic layer is washed with 2N NaOH, water, brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is purified via chromatography
  9. washeluting with 5:1 hexane

Sources & evidence

ORD record
ord-ab9821b7930a4840ab779b1a13f174d5
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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