Iodine → 3-(3-iodo-4-methoxybenzyl)-1H-1,2,4-triazole

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][C:8]2[N:12]=[CH:11][NH:10][N:9]=2)=[CH:5][CH:4]=1.[I:15]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:15][C:14]1[CH:13]=[C:6]([CH:5]=[CH:4][C:3]=1[O:2][CH3:1])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][N:9]=1

Participants

Procedure

To a solution of 3-(4-methoxybenzyl)-1H-1,2,4-triazole (335 mg, 1.770 mmol) in MeOH (5 ml) under nitrogen at RT was added silver sulfate (552 mg, 1.770 mmol) followed by iodine (449 mg, 1.770 mmol). Added a second equivalent of silver sulfate and stirred for 3 days. The reaction did not go to completion. The solids were filtered washing with MeOH, the filtrate was concentrated, and the residue was purified by flash column chromatography on silica gel, eluting with MeOH in DCM to afford the title compound contaminated with ca. 20% of starting material. Mass spectrum (ESI) 316.1 (M+1).