反应详情

温度

80 °C

5-Bromo-6-(isobutylthio)picolinic acid (500 mg, 1.72 mmol) was dissolved in methanol (5 mL) to give a yellow solution. Sulfuric acid (169 mg, 92.3 μL, 1.72 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 1 d. The reaction mixture was cooled to 0° C. and poured onto icewater/brine (25 mL). The aqueous layer was extracted with EtOAc (2×40 mL) and washed with icewater/brine (20 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give crude title compound as a yellow oil. The oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane) to give the title product (205 mg, 39%) as a colorless oil. MS (EI): m/e=306.3 [M+H]+.

1. customto give a yellow solution
2. temperatureThe reaction mixture was cooled to 0° C.
3. extractionThe aqueous layer was extracted with EtOAc (2×40 mL)
4. washwashed with icewater/brine (20 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. customto give crude title compound as a yellow oil
8. customThe oil was purified by flash chromatography (silica gel, 5 g, 0% to 15% EtOAc in heptane)