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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 116241-61-3, name is 2-Fluoro-6-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. name: 2-Fluoro-6-methoxypyridine
A Schlenk flask with a stir bar was charged with NaOMe (4.7g, 87mmol) and sealed with a rubber septum, and THF (200mL) was added via cannula. Under N2(g) atmosphere, 2,6-difluoropyridine (5.0g, 43mmol) was added dropwise to the stirring solution via syringe to form 2-(methoxy)-6-fluoropyridine. This reaction was stirred overnight (approximately 12h) then THF was removed under reduced pressure. The flask containing crude product was evacuated and under positive N2(g), approximately 100mL of DMF was added, followed by the addition of imidazole (3.575g, 52.5mmol) and NaH (1.9g, 160mmol) at 0C. The flask was allowed to warm to room temperature and with positive nitrogen flow, a reflux condenser was attached and the flask was heated to 80C overnight with stirring. The reaction flask was cooled to room temperature, the DMF was removed from the mixture via rotary evaporator, and the remaining reaction mixture was transferred to a separatory funnel with 25mL CH2Cl2. The organic phase was washed with water (25mL x 3), dried over MgSO4, filtered, and the filtrate was concentrated to dryness via rotary evaporator. The crude Im-pyOMe was dissolved in 200mL of DMF and ethyl bromide (5.2g, 48mmol) was added dropwise with stirring. Under positive pressure of N2(g), a reflux condenser was attached and the flask was heated to 120C overnight. The reaction flask was cooled to room temperature and the red oily product was obtained after solvent removal. Upon column chromatography purification with 90:10 ratio of MeOH: CH2Cl2, 42% (5.233g, 18.4mmol) of product was obtained. 1H NMR (360MHz, CDCl3, ppm): delta 11.60 (s, 1H), 8.16 (t, 1H, Im, 3JHH=1.8Hz), 7.88 (t, 1H, py, 3JHH=8.0Hz), 7.46 (t, 1H, Im, 3JHH=1.8Hz), 7.93 (d, 1H, py, 3JHH=8.1Hz), 6.86 (d, 1H, py, 3JHH=8.1Hz), 4.67 (q, 2H, CH2CH3, 3JHH=7.4Hz), 1.73 (t, 3H, CH2CH3, 3JHH=7.4Hz), 4.03 (s, 3H, OCH3). 13C NMR (125.76MHz, CDCl3, ppm): delta 164.26 (py), 144.11 (py), 142.64 (py), 135.10 (im), 123.12 (im), 119.50 (im), 112.35 (py), 106.58 (py), 54.91 (OMe), 46.51 (NCH2CH3 of cationic imidazolium), 16.25 (NCH2CH3 of cationic imidazolium). EI-MS (EI+): m/z 176.1 (Im-pyOMe)+.
If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 116241-61-3, 2-Fluoro-6-methoxypyridine.
Reference:
Article; Gerlach, Deidra L.; Siek, Sopheavy; Burks, Dalton B.; Tesh, Jamie M.; Thompson, Courtney R.; Vasquez, Robert M.; White, Nicholas J.; Zeller, Matthias; Grotjahn, Douglas B.; Papish, Elizabeth T.; Inorganica Chimica Acta; vol. 466; (2017); p. 442 – 450;,
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