Dimethylformamide → 5-Bromo-2-(1-methyl-1H-1,2,4-triazol-5-yl)thiazole

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl-5-thiazol-2-yl-1H-[1,2,4]triazole (6.55 g; 39 4 mmol) and dimethylformamide (32 mL), add N-bromosuccinimide (14 g, 78.8 mmol) in three portions over 1 h. Stir the mixture at 22° C. for 18 h and then add to water (300 mL) chilled to 0-5° C. Separate the aqueous layer and extract with methyl-t-butyl ether (2×200 mL). Combine the organic layers and wash with 7% aqueous sodium hydrogen carbonate (100 mL) and then dry over sodium sulfate. Filter and evaporate the solvent to afford the title compound (9.5 g, 93%). ES/MS m/z (79Br/81Br) 245/247 (M+1)+.

Provenance & Evidence