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To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 ml_) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 °C. The reaction mixture was allowed to stir for 10h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 ml_).The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5 percent ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 percent).
97%
at 60℃; for 10 h;
To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 °C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulphate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5 percent ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 percent).
97%
With phosphorus pentachloride; trichlorophosphate In hexane; ethyl acetate at 60℃; for 10 h;
Step 1: To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60° C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5percent ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97percent).
97%
With phosphorus pentachloride; trichlorophosphate In hexane at 60℃; for 10 h;
Step 1 To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60° C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5percent ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97percent).
With phosphorus pentachloride; trichlorophosphate; at 60℃; for 10h;
To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 ml_) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 ml_).The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5 % ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 %).
97%
With phosphorus pentachloride; trichlorophosphate; at 60℃; for 10h;
To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3 x 20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulphate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5 % ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97 %).
97%
With phosphorus pentachloride; trichlorophosphate; In hexane; ethyl acetate; at 60℃; for 10h;
Step 1: To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to ambient temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using silica gel column chromatography (100-200 mesh, 5% ethyl acetate in hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97%).
97%
With phosphorus pentachloride; trichlorophosphate; In hexane; at 60℃; for 10h;
Step 1 To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorous oxychloride (15 mL) was added phosphorous pentachloride (2.96 g, 14.22 mmol) at 60 C. The reaction mixture was allowed to stir for 10 h at the same temperature. The reaction mixture was cooled to room temperature and was poured into crushed ice and was extracted with ethyl acetate (3*20 mL). The total organic layer was washed with saturated sodium carbonate solution (25 mL). The washed organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure to obtain crude compound which was purified by using column chromatography (silica gel: 100-200 mesh, eluent: 5% ethyl acetate in n-hexane) to afford 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97%).
With sulfuric acid; nitric acid; at 25 - 80℃; for 2h;
Into a 2000-mL round-bottom flask was placed 3-fluoro-l,2-dihydropyridin-2- one (100 g, 884.22 mmol, 1.00 equiv), and con. H2S04 (700 mL), by the dropwise addition of fuming HNCb (150 mL) while stirring at 80 C. The resulting solution was stirred for 2 h at 25 C. The reaction progress was monitored by LCMS. The reaction was poured into 5000 mL of water/ice. The resulting solution was extracted with 3x2000 mL of ethyl acetate. The resulting mixture was concentrated under vacuum. The crude product was crystallized from ethyl acetate to give 40 g (30% yield) of 3-fluoro-5-nitro-l,2- dihydropyridin-2-one as a yellow solid. LCMS (ESI): RT= 0.49 min, m/z =159 [M+H]+; NMR (300 MHz, Methanol- cUppm) d 8.52 (dd, J= 2.8, 1.1 Hz, 1H), 8.09 (dd, J= 10.0, 2.8 Hz, 1H)
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