Ethyl 2,6-dichloro-5-fluoro-pyridine-3-acetoacetate synthesis
- Product Name:Ethyl 2,6-dichloro-5-fluoro-pyridine-3-acetoacetate
- CAS Number:96568-04-6
- Molecular formula:C10H8Cl2FNO3
- Molecular Weight:280.08
6148-64-7
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82671-02-1
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96568-04-6
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Yield:96568-04-6 80%
Reaction Conditions:
Stage #1:ethyl potassium malonate;2,6-dichloro-5-fluoro-pyridine-3-carbonitrile with zinc(II) chloride in 1,2-dichloro-ethaneHeating / reflux;
Stage #2: with hydrogenchloride;water in 1,2-dichloro-ethane at 90; for 4 h;Product distribution / selectivity;
Steps:
2
EXAMPLE 2 Preparation of ethyl 3-(2,6-dichloro-5-fluoro-3-pyridyl)-3-oxopropanoate To 100 of 1,2-dichloroethane were added 10 g of 2,6-dichloro-5-fluoro-3-cyanopyridine, 3.6 g of zinc chloride, and 11 g of potassium ethylmalonate, and then the mixture was stirred at reflux. After the reaction was completed, 50 of 6 N hydrochloric acid was added to the mixture, which then was stirred at reflux at 90° C. for 4 hours. After confirming completion of the reaction by TLC, the solution was cooled to 20° C., and then an organic layer was separated therefrom. The organic layer was dried through distillation under reduced pressure, and 50 of a mixed solvent of ethanol and water (7:3, v/v) was added thereto. Then, the reactor was cooled to 0~10° C., and was stirred for 1 hour. The resulting solid was filtered and washed with 25 of a mixed solvent of ethanol and water (7:3, v/v) having the same temperature, to obtain the title compound in the yield of 80% (11.7 g) 1H NMR (400 MHz, CDCl3) δ Enol Form(80%): 12.55 (s, 1 H), 7.82 (d, J=7.6 Hz, 1 H), 5.81 (s, 1 H), 4.27 (q, J=7.2 Hz, 2 H), 1.33 (t, J=7.2 Hz, 3 H). Keto Form (20%): 7.82 (d, J=7.6 Hz, 1 H), 4.18 (q, J=7.2 Hz, 2 H), 4.08 (s, 2 H), 1.24 (t, J=7.2 Hz, 3 H). Mass (APCI, m/z): 278 (M-H, 43), 264 (38), 232 (24), 214 (100).
References:
Shin, Hyun Ik;Choi, Bo Seung;Lee, Jae Hoon US2008/221333, 2008, A1 Location in patent:Page/Page column 3
![Propanedioic acid, 2-[(2,6-dichloro-5-fluoro-3-pyridinyl)carbonyl]-, 1,3-diethyl ester](/CAS/20210305/GIF/96568-03-5.gif)
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