Trifluoroacetic anhydride → 2-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

HRID 623709Notes

Reaction equation

HRID 623709 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH3:14])[C:11]([CH3:15])=[N+:10]1[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:20]>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[N:13]=[C:12]([CH2:14][OH:20])[C:11]([CH3:15])=[N:10]1

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 901098102-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide2×

Product 1

HCID 901092522-(2,4-Difluorophenyl)-5-methyl-2H-1,2,3-triazole-4-methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(2,4-difluorophenyl)-4,5-dimethyl-2H-1,2,3-triazole 1-oxide (i.e. the product of Step A, 1.78 g, 7.0 mmol) in tetrahydrofuran (14 mL) was added trifluoroacetic anhydride (2.5 mL, 17.5 mmol). The reaction mixture was stirred at 110° C. in the microwave for 75 min. The mixture was diluted with ethyl acetate, washed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide, dried (MgSO4) and concentrated under reduced pressure to afford the crude product. The crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes to obtain the title compound (0.59 g) as a colorless solid.

Workup

  1. washwashed successively with 1.0 M aqueous sodium hydroxide and 50% aqueous sodium hydroxide
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product
  5. customThe crude material was purified by chromatography on silica gel eluting with 0 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9ac76b9069f9454cbc7121c5c424d5ac
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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