Brief introduction of 1-(3-Fluoropyridin-4-yl)ethanol

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87674-15-5, its application will become more common.

Electric Literature of 87674-15-5 ,Some common heterocyclic compound, 87674-15-5, molecular formula is C7H8FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 2; 2-Bromo-1 -(3«fluoropyridin-4-yl)ethanone hydrobromide; Into a stirred solution of 3-fluoropyridine (14 g, 144.2 rnmol) in anhydrous THF (150 mL), cooled to -780C and under argon, 79.2 mL (158.6 mmol) of a 2N solution of lithiumdiisopropylamsde (LDA) in n-heptane, THF, ethylbenzene, were slowly dropped in about 1h. After stirring for 2.5h a cooled solution (ca. 0DC) of acetaldehyde (8.9 mL, 158.5 mmot) in 25 mL of anhydrous THF was slowly dropped and the reaction mixture was stirred at -78C for 1.5 h. The solution was warmed to -30C and a solution of ammonium chloride (15Og) in 700 mL of water was added. The mixture was extracted with ethylacetate (3 x 400 ml_) and the organic layers were washed with brine (4 x 200 mL) and dried over sodium sulfate. After concentration, the oil was crystallized with n-hexane (40 mL) and 15.6 g (76% yield) of 1-{3- fiuoropyridin-4-yl)ethanol were obtained. A mixture of 1-(3-fiuoropyridin-4-y.)ethanoi (10 g, 70.3 mrnol) and commercial activated MnO2 (8 g, 92.1 mmol) in toluene (100 mL) were refluxed until disappearance of starting material. After cooling, the mixture was filtered on a bed of celite, the cake washed with toluene and the organic phases concentrated to give 3- f.uoro-4-acetyi pyridine (6.9 g, 70%) that was used directly in the next step. To a stirred solution of 3-flu?ro-4-acetyipyridine (5.3 g, 38.1 mmol} in glacial acetic acid (14 mL) and 48% hydrobromic acid (5.3 mL), bromine (2 mL, 38 mmol) in glacial acetic acid (5.3 mL) was added slowly and dropwise. After addition, the solution was stirred at 60DC for 2.5 hour. This solution was cooled down and ethylacetate (70 mL) was added. After 30 minutes of stirring, the mixture was filtered and the solid was washed thoroughly with ethylacetate and dried. The title compound was obtained in 82% yield (9.4 g).1H NMR (DMSOd6 /400 MHz) delta ppm 4.88 (s, 2 H) 7.83 (dd, 1 H) 8.62 (dd, 1 H) 8.81 (d, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,87674-15-5, its application will become more common.

Reference:
Patent; PFIZER ITALIA SRL; WO2007/96334; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem