Hydrochloric Acid → 3,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-ol

HRID 2198767Notes

Reaction equation

HRID 2198767 reaction equation
[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[C:4](=[O:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[N:9][CH:8]=[N:7]1.[BH4-].[Na+].Cl>CO>[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[CH:4]([OH:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[N:9][CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 12899882HCID 12899882, compound

Product 1

HCID 128998833,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-olYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

130.5 g (0.395 mol) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-2-butanone were dissolved in 800 ml of methanol, and 21 g (0.55 mol) of sodium borohydride were added in portions. The reaction solution was subsequently stirred for 15 hours and was then adjusted to a pH value of 3 with concentrated hydrochloric acid. The mixture was then stirred for 2 hours. After distilling off the solvent in vacuo, water/sodium bicarbonate were added to the residue and the mixture was extracted by shaking with 600 ml of methylene chloride. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. The residue was crystallized with diisopropyl ether. 112 g (86% of theory) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-ol of melting point 97°-102° C. were obtained. ##STR77##

Workup

  1. stirringThe mixture was then stirred for 2 hours
  2. distillationAfter distilling off the solvent in vacuo, water/sodium bicarbonate
  3. additionwere added to the residue
  4. extractionthe mixture was extracted
  5. stirringby shaking with 600 ml of methylene chloride
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-34533da1e57c499abd5a89384401178b
Source dataset
uspto-grants-1982_11
Patent number
US04359470

Reaction notes

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