(Diethylamino)sulfur trifluoride → 4-(fluoromethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole

HRID 623706Notes

Reaction equation

HRID 623706 reaction equation
[F:1][C:2]([F:29])([F:28])[O:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][C:8]1[C:9]([CH2:23]O)=[N:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:12]=1.C(N(S(F)(F)[F:36])CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[F:36][CH2:23][C:9]1[C:8]([O:7][C:6]2[CH:25]=[CH:26][CH:27]=[C:4]([O:3][C:2]([F:28])([F:29])[F:1])[CH:5]=2)=[N:12][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:22])[F:20])=[CH:15][CH:14]=2)[N:10]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 901115035-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol2×

Product 1

HCID 901089054-(fluoromethyl)-5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-30 °C

Procedure

To a stirred solution of 5-[3-(trifluoromethoxy)phenoxy]-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole-4-methanol (i.e. the product of Example 5, Step I, 0.075 g, 0.18 mmol) in anhydrous dichloromethane (4 mL) cooled to −78° C. was added (diethylamino)sulfur trifluoride (0.032 mL, 0.24 mmol). The mixture was stirred for 2 h during which time the temperature increase to −30° C. The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (5 mL), extracted with ethyl acetate (3×15 mL), and washed with saturated aqueous sodium chloride solution (10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford the crude product which was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to obtain the title compound (0.052 g) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (3×15 mL)
  2. washwashed with saturated aqueous sodium chloride solution (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product which
  6. customwas purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-2db5f57bb7924ae1a21b3a6ba6b5a276
Source dataset
uspto-grants-2016_04
Patent number
US09302999B2

Reaction notes

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