Potassium Carbonate → 4-(4,4-Difluorobut-3-enylthio)-1,2,3-benzotriazine

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Reaction Steps

The product of Step 1 (1 g), 4-bromo-4,4-difluorobutyl methanesulfonate (1.65 g) and potassium carbonate (0.852 g) were stirred together in acetone (30 cm3) at ambient temperature for 36 hours. Inorganic solids were removed by filtration and the filtrate evaporated under reduced pressure to give a brown oil. Chromatography on silica gel using 1:4 ethyl acetate:hexane as eluant gave two yellow oils (ea 0.5 g). The first-eluted oil was identified as N-alkylated material and the second was the desired S-alkyated intermediate 4-(4-bromo-4,4-difluorobutylthio)-1,2,3-benzotriazine. 1H NMR: δ 2.18-2.31 (2H,m); 2.58-2.71 (2H,m); 3.63(2H,t); 7.95(1H,t); 8.09(2H,m); 8.40(1H,d).

Provenance & Evidence