反应详情

温度

12.5 °C

To a solution of para-toluenesulfonic acid monohydrate (510 mg, 2.68 mmol) in acetonitrile (3.5 mL), was added 4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-amine (253 mg, 0.893 mmol). The resulting suspension was cooled to 10-15° C. and treated with an aqueous solution of sodium nitrite (537 μl, 1.787 mmol) and potassium iodide (536 μl, 2.23 mmol). The mixture was stirred for 10 minutes at 0° C. and then warmed to ambient temperature. The mixture was diluted with water and treated with sodium bicarbonate (1 M, aqueous) until the mixture was adjusted to pH 9-10, which was followed by treatment of a 3 M aqueous solution of Na2S2O3 (6 mL). The solid was collected by filtration and washed with cold diethyl ether and hexane. The residue was purified via silica gel chromatography (ethyl acetate/hexane gradient), providing the titled compound: 1H NMR (500 MHz, CDCl3) 7.86 (d, 1H, J=8.7 Hz), 7.25 (d, 1H, J=9.0 Hz), 4.36 (s, 2H), 1.04 (s, 9H) ppm. LRMS m/z (M+H) 393.8 and 395.8 found, 393.9 and 395.9 required.

1. temperaturewarmed to ambient temperature
2. filtrationThe solid was collected by filtration
3. washwashed with cold diethyl ether and hexane
4. customThe residue was purified via silica gel chromatography (ethyl acetate/hexane gradient)