2-Chloro-3-fluoro-5-nitropyridine synthesis
- Product Name:2-Chloro-3-fluoro-5-nitropyridine
- CAS Number:1079179-12-6
- Molecular formula:C5H2ClFN2O2
- Molecular Weight:176.53
1033202-14-0
1079179-12-6
General procedure for the synthesis of 2-chloro-3-fluoro-5-nitropyridine from 3-fluoro-5-nitropyridin-2(1H)-one: To a stirred solution of 3-fluoro-5-nitropyridin-2-ol (1.5 g, 9.48 mmol) in phosphorus trichloride (15 mL) was slowly added phosphorus pentachloride (2.96 g, 14.22 mmol) at 60 °C. The reaction mixture was kept continuously stirred at 60 °C for 10 hours. After the reaction was completed, the mixture was cooled to room temperature and carefully poured into crushed ice. Extraction was carried out with ethyl acetate (3 x 20 mL). The organic layers were combined and washed with saturated sodium carbonate solution (25 mL) and subsequently dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by silica gel column chromatography (100-200 mesh, eluent 5% ethyl acetate in hexane solution) to afford the target compound 2-chloro-3-fluoro-5-nitropyridine (1.62 g, 97% yield).
1033202-14-0
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Yield:1079179-12-6 97%
Reaction Conditions:
with phosphorus pentachloride;trichlorophosphate at 60; for 10 h;
Steps:
67.1 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 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 %).
References:
GRüNENTHAL GMBH;FRANK, Robert;CHRISTOPH, Thomas;LESCH, Bernhard;LEE, Jeewoo WO2013/13817, 2013, A1 Location in patent:Page/Page column 96; 97
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