Acetaldehyde → 1-(3-Bromo-1-methyl-1H-1,2,4-triazol-5-YL)ethan-1-OL

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Reaction Conditions

Reaction Steps

To a solution of 3,5-dibromo-1-methyl-1H-1,2,4-triazole (2.634 g, 10.9 mmol, Eq: 1.00) in tetrahydrofuran (184 ml) was added dropwise at −78° C. under argon atmosphere n-butyllithium 1.6 M in hexanes (6.83 ml, 10.9 mmol, Eq: 1.00). The resulting mixture was stirred for 20 minutes at −75° C. then a solution of acetaldehyde (1.2 g, 1.54 ml, 27.3 mmol, Eq: 2.5) in tetrahydrofuran (36.9 ml) was added slowly and stirring at −75° C. was continued for further 1.5 hours. The mixture was quenched with sat. aq. NH4Cl solution and was warmed to 25° C. The mixture was diluted with ethyl acetate and washed 2 times with water. The organic layer was separated, dried over magnesium sulfate, filtrated and evaporated affording 1-(5-bromo-2-methyl-2H-[1,2,4]triazol-3-yl)-ethanol (1.639 g, 72.7%) as a light yellow oil. MS: m/z=206209 (M+H+)

Provenance & Evidence