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

HRID 631907Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][Si](C)(C)C)[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:18])[N:8]=[N:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

distillationVolatiles were distilled off
customcrude mass was purified by normal silica gel column chromatography
washas eluting solvent

Sources & evidence

ORD record: ord-84bf16375ada4541b12efff75398fb66
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321738B2

Reaction notes

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