Water → 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

To a stirred solution of 5-(4-bromo-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (1.9 g, 4.974 mmol) in THF (40 mL), was added water (0.18 mL, 9.948 mmol) and cooled to 0° C. Then TBAF (1M) solution in THF (5.9 mL, 5.9 mmol) was added and the mixture was stirred at 0° C. for 10 min. Volatiles were distilled off and crude mass was purified by normal silica gel column chromatography using EtOAc-hexane as eluting solvent to get 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (0.7 g, 45.42% yield) as an off white solid. LC-MS: 310 (M+H); 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=7.0 Hz, 3H), 4.27 (s, 3H), 4.31 (q, J=7.0 Hz, 2H), 7.68 (s, 4H). The regio-chemistry was confirmed by NOE study.

Provenance & Evidence