Benzyl Bromide → 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester

Participants

Reaction Steps

To a suspension of 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid (209 mg, 0.74 mmol) and sodium bicarbonate (187 mg, 2.22 mmol) in DMF (10 mL) was added an excess of benzyl bromide (380 mg, 264 μL, 2.22 mmol) at room temperature under nitrogen atmosphere. The resulting colorless reaction mixture was stirred for 15 h at which time LC/MS and TLC analysis indicated the absence of starting material. The mixture was diluted with water and extracted with ethyl acetate (2×70 mL). The combined extracts were washed with brine solution and dried over anhydrous MgSO4. Filtration and concentration gave the crude colorless oil which was purified using an ISCO (40 g) column chromatography eluting with ethyl acetate in hexanes (0-60%). The desired fractions were collected and the solvent was removed under vacuum to isolate the 5-(4-bromophenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester as a viscous oil (275 mg, 99% yield). LC/MS calcd. for C17H14BrN3O2 (m/e) 373, obsd. 373.8 [M+H, ES+].

Provenance & Evidence