2-Iodobenzoic acid → 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF was treated with 1,2,3-triazole (1.5 g, 21.7 mmol), Cs2CO3 (7.08 g, 21.7 mmol), CuI (114 mg, 0.60 mmol), and trans-N,N′-dimethylcyclohexane-1,2-diamine (310 mg, 2.17 mmol). The mixture was heated at 120° C. for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with EtOAc, and filtered through Celite®. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH/DCM with 0.1% AcOH) to provide the faster eluting title compound as a white solid. Data for D-1: 1H NMR (500 MHz, DMSO-d6) δ 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H). The undesired 1-(2H-1,2,3-triazol-2-yl)benzoic acid (D-2) eluted second. 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (D-3) was prepared in an analogous manner.

Provenance & Evidence