Reaction #2320147

Reaction equation

1-Azido-2,3-dichlorobenzene

3-phenyl-1-propyne

→

title compound

5-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,3-triazole

Solvents

toluene

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   Concentrationconcentrated under reduced pressure
3. 3
   Otherto give
4. 4
   workup.ADDITIONa mixture of regioisomers
5. 5
   OtherThe residue was purified by flash chromatography
6. 6
   Washeluting with hexanes:ethyl acetate (3:1)

Procedure

1-Azido-2,3-dichlorobenzene (200 mg, 1.06 mmol) (Cambie J. Organomet. Chem. 1996, 507, 1) and 3-phenyl-1-propyne (150 μL, 1.1 equiv) were combined in toluene (0.2 mL) and heated at 100° C. for 18 hours, allowed to cool to room temperature, and then concentrated under reduced pressure to give a mixture of regioisomers. The residue was purified by flash chromatography eluting with hexanes:ethyl acetate (3:1) to provide the title compound. MS (DCI/NH3) m/z 304 (M+H)+; 1H NMR (CDCl3) δ 3.87 (br s, 2H), 6.98 (m, 2H), 7.13 (dd, 1H), 7.22 (m, 3H), 7.29 (t, 1H), 7.56 (s, 1H), 7.64 (dd, 1H).

Source