반응 #1130627

반응 방정식

potassium permanganate

potassium permanganate

NaNO2

H2SO4

2-fluoro-3-[(4-fluoro-2-nitrophenyl)ethynyl]pyridine

sodium bicarbonate

magnesium sulfate

water

→

desired product

1-(4-fluoro-2-nitrophenyl)-2-(2-fluoropyridin-3-yl)ethane-1,2-dione

용매

acetone

반응 조건

후처리

1. 1
   기타A 250 mL Erlenmeyer flask, immersed in a water bath at 25° C.
2. 2
   workup.STIRRINGthe mixture was stirred for 4 hours
3. 3
   기타separating funnel
4. 4
   추출saturated with NaCl, and extracted with ethyl acetate 2×
5. 5
   건조dried over MgSO4
6. 6
   농축concentrated
7. 7
   기타was purified by column chromatography on silica gel

실험 절차

A 250 mL Erlenmeyer flask, immersed in a water bath at 25° C., was charged with acetone (20 mL) and 2-fluoro-3-[(4-fluoro-2-nitrophenyl)ethynyl]pyridine (0.443 g, 0.0017 mol). To this solution was added a solution of sodium bicarbonate (0.08 g, 0.001 mol) and magnesium sulfate (0.4 g, 0.003 mol) in water (10 mL). The mixture was stirred with a mechanical stirrer. Powdered potassium permanganate (0.91 g, 0.0058 mol) was then added in one portion, and the mixture was stirred for 4 hours. The unreacted potassium permanganate and the precipitated MnO2 were reduced to soluble Mn2+ ions by adding a minimum quantity of NaNO2 (0.14 g) and 10% H2SO4 (1.4 mL) in small portions. The solution was transferred to a 250 mL separating funnel, saturated with NaCl, and extracted with ethyl acetate 2×, dried over MgSO4, concentrated and was purified by column chromatography on silica gel. (20% ethyl acetate, 80% hexanes) to give 0.45 g of the desired product. 1H NMR (400 MHz, CDCl3): δ 8.51-8.53 (m, 1H), 8.41-8.46 (m, 1H), 7.88-7.95 (m, 2H), 7.58-7.62 (m, 1H), 7.41-7.45 (m, 1H). MS [M+H]=292.9.

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