Benzylacetylene → 5-benzyl-1-(2,3-dichlorophenyl)-1H-1,2,3-triazole
Reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[Cl:11])=[N+:2]=[N-:3].[C:12]1([CH2:18][C:19]#[CH:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[CH2:18]([C:19]1[N:1]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=2[Cl:11])[N:2]=[N:3][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
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).