Diethyl Ether → Methyl 4-(1,2,4-triazol-1-yl)-2-trifluoromethylbenzoate

HRID 1601713Notes

Reaction equation

HRID 1601713 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CN(C)C=O>[N:16]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]([F:15])([F:14])[F:13])[CH:3]=2)[CH:20]=[N:19][CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 15541084Methyl 4-fluoro-2-(trifluoromethyl)benzoate

Product 1

HCID 18795041Methyl 4-(1,2,4-triazol-1-yl)-2-trifluoromethylbenzoateYield 83.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-fluoro-2-trifluoromethylbenzoate (4.95 g) in N,N-dimethylformamide was added 1,2,4-triazole (2.0 g) and potassium carbonate (4.0 g) at 20° C. and the mixture stirred for 4 hours at 60° C. The mixture was diluted (ether), washed (aqueous citric acid) and dried (magnesium sulfate). The residue was purified by chromatography to give methyl 4-(1,2,4-triazol-1-yl)-2-trifluoromethylbenzoate (5.07 g), NMR 3.98(s,3H),7.94-8.05(2H),8.15(2H),8.71 (s,1H).

Workup

  1. washwashed (aqueous citric acid)
  2. dry with materialdried (magnesium sulfate)
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-8f62f011ae7b48fe88a40c9af20f1cf5
Source dataset
uspto-grants-1999_11
Patent number
US05977376

Reaction notes

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