Water → 2-[2'-Difluoromethoxy-4'-chlorophenyl]-2-(1h-1,2,4-triazolylmethyl)-4-ethyl-1,3-dioxolane

HRID 1721922Notes

Reaction equation

HRID 1721922 reaction equation
[Na].[NH:2]1[CH:6]=[N:5][CH:4]=[N:3]1.[I-].[K+].[F:9][CH:10]([F:28])[O:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1([CH2:26]Br)[O:23][CH:22]([CH2:24][CH3:25])[CH2:21][O:20]1.O>CN(C)C=O>[F:28][CH:10]([F:9])[O:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[C:19]1([CH2:26][N:2]2[CH:6]=[N:5][CH:4]=[N:3]2)[O:23][CH:22]([CH2:24][CH3:25])[CH2:21][O:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 230432922-(2'-Difluoromethoxy-4'-chlorophenyl)-2-bromomethyl-4-ethyl-1,3-dioxolaneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 230432942-[2'-Difluoromethoxy-4'-chlorophenyl]-2-(1h-1,2,4-triazolylmethyl)-4-ethyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.9 parts of 1,2,4-triazole sodium salt, a catalytic amount of potassium iodide and 12 parts of the 2-(2'-difluoromethoxy-4'-chlorophenyl)-2-bromomethyl-4-ethyl-1,3-dioxolane prepared in (b) are stirred in 100 ml of dimethylformamide for 16 hours at a bath temperature of 130° C. The reaction mixture is cooled to room temperature, poured into 500 ml of water and extracted with 2×300 ml of diethyl ether. The combined organic phases are washed with 2×200 ml of water, dried over sodium sulfate, filtered, and the solvent is removed by evaporation. The oily residue is chromatographed through a 50 cm column of silica gel with a 1:1 mixture of methylene chloride/diethyl ether as eluant. The eluant is removed by evaporation to give a yellow oil with a refractive index nD27 : 1.5132.

Workup

  1. extractionextracted with 2×300 ml of diethyl ether
  2. washThe combined organic phases are washed with 2×200 ml of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation
  6. customThe oily residue is chromatographed through a 50 cm column of silica gel with a 1:1 mixture of methylene chloride/diethyl ether as eluant
  7. customThe eluant is removed by evaporation
  8. customto give a yellow oil with a refractive index nD27

Sources & evidence

ORD record
ord-a1f93e66e4d44be89a51e300b59a1f71
Source dataset
uspto-grants-1989_08
Patent number
US04853399

Reaction notes

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