Pyridine → HCID 12182452, compound

HRID 1196645Notes

Reaction equation

HRID 1196645 reaction equation
[Na].[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[OH:10].N1C=CC=CC=1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1>COCCOCCOC.[Cu].[Cu]I>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[O:10][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 77304-BromoanisoleHCID 1230512,4-DifluorophenolHCID 5360545Sodium

Product 1

HCID 12182452HCID 12182452, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8150DiglymeSolvent

Procedure

To a suspension of the anhydrous sodium salt of 206 g of 2,4-difluorophenol in 400 ml of diethylene glycol dimethyl ether are added 5 g of copper powder, 5 g of copper(I) iodide, 8 ml of pyridine and 393 g of 4-bromoanisole. With stirring, the reaction mixture is heated, under nitrogen, for 17 hours to 150°-155° C. After cooling, the reaction mixture is filtered over Hyflo and the bulk of the solvent is removed by vacuum distillation. The residue is dissolved in ether and the ethereal solution is washed repeatedly with 10% aqueous sodium hydroxide and then with water. The ethereal solution is dried over sodium sulfate and the solvent is removed by distillation. The residue is purified by chromatography over silica gel (eluant: 8:1 mixture of petroleum ether/diethyl ether). The solvent is removed by evaporation, to give the title compound in the form of a residual oil; nD22 =1.5466.

Workup

  1. temperaturethe reaction mixture is heated, under nitrogen, for 17 hours to 150°-155° C
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered over Hyflo
  4. customthe bulk of the solvent is removed by vacuum distillation
  5. dissolutionThe residue is dissolved in ether
  6. washthe ethereal solution is washed repeatedly with 10% aqueous sodium hydroxide
  7. dry with materialThe ethereal solution is dried over sodium sulfate
  8. customthe solvent is removed by distillation
  9. customThe residue is purified by chromatography over silica gel (eluant: 8:1 mixture of petroleum ether/diethyl ether)
  10. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-2821d6f0c8714408aac53559240367be
Source dataset
uspto-grants-1992_05
Patent number
US05114977

Reaction notes

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