2-Chloromethyl-2-(2-fluoro-4-trifluoromethylphenyl)oxirane → 2-(2-Fluoro-4-trifluoromethylphenyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane

HRID 1732152Notes

Reaction equation

HRID 1732152 reaction equation
Cl[CH2:2][C:3]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=2[F:16])[CH2:5][O:4]1.[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1.[Na]>C(O)(C)(C)C>[F:16][C:7]1[CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=[CH:11][C:6]=1[C:3]1([CH2:2][N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)[CH2:5][O:4]1

Participants

4

Reactant 2

HCID 202267062-Chloromethyl-2-(2-fluoro-4-trifluoromethylphenyl)oxiraneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 202266732-(2-Fluoro-4-trifluoromethylphenyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 2-chloromethyl-2-(2-fluoro-4-trifluoromethylphenyl)oxirane (6 g.) in tert-butyl alcohol was treated with sodium 1,2,4-triazole (2.7 g.) and heated at 100° for 1 hour. The mixture was evaporated and the residual gum partitioned between ethyl acetate and water. the organic layer was washed with water, dried and evaporated to dryness. The residual gum was chromatographed on K60 silica gel using chloroform/petroleum ether (b.p. 60°-80°) 1:1 v/v and chloroform as eluting solvents to give 2-(2-fluoro-4-trifluoromethylphenyl)-2-(1,2,4-triazol-1-ylmethyl)oxirane, as a gum with NMR data as follows:

Workup

  1. temperatureheated at 100° for 1 hour
  2. customThe mixture was evaporated
  3. customthe residual gum partitioned between ethyl acetate and water
  4. washthe organic layer was washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residual gum was chromatographed on K60 silica gel
  8. washas eluting solvents

Sources & evidence

ORD record
ord-738947c28531464abb32b4ecf161b996
Source dataset
uspto-grants-1986_11
Patent number
US04625036

Reaction notes

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