Phenylacetylene → 4-Phenyl-1-[[3-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazole

HRID 1424677Notes

Reaction equation

HRID 1424677 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]([F:22])([F:21])[C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[CH2:14][N:15]=[N+:16]=[N-:17].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.[O-]S([O-])(=O)=O.[Cu+2]>[C:1]1([C:7]2[N:17]=[N:16][N:15]([CH2:14][C:13]3[CH:18]=[CH:19][CH:20]=[C:11]([C:10]([F:9])([F:22])[F:21])[CH:12]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10821PhenylacetyleneHCID 212826681-(Azidomethyl)-3-(trifluoromethyl)benzeneHCID 23667548Sodium Ascorbate

Product 1

HCID 669580594-Phenyl-1-[[3-(trifluoromethyl)phenyl]methyl]-1H-1,2,3-triazoleYield 92%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

Route B: Phenylacetylene (0.409 g, 4 mmol) and 3-(trifluoromethyl)benzyl azide (0.805 g, 4.00 mmol) were dissolved in 4:1 t-BuOH/H2O (25 ml) and then treated sequentially with a 1M aq. solution of CuSO4 (0.200 ml, 0.200 mmol) followed by solid sodium ascorbate (0.079 g, 0.400 mmol). The sample was stirred at r.t. for 4 h. during which time a precipitate formed. The sample was quenched with 10 mL of 10% NH4OH aq. and the solid was isolated by filtration. The solid was washed with water and dried under vacuum, giving 4 (1.112 g, 3.67 mmol, 92% yield) as a white solid.

Workup

  1. customformed
  2. customThe sample was quenched with 10 mL of 10% NH4OH aq.
  3. customthe solid was isolated by filtration
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fa339fa987ec4ed58dc7cc3364e0dda1
Source dataset
uspto-grants-2015_01
Patent number
US08927736B2

Reaction notes

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