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Chemical Structure| 915720-54-6

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Product Details of [ 915720-54-6 ]

CAS No. :915720-54-6
Formula : C7H6FNO
M.W : 139.13
SMILES Code : CC(=O)C1=NC=C(F)C=C1
MDL No. :MFCD10698609
InChI Key :VSPHPRHMHNAYBJ-UHFFFAOYSA-N
Pubchem ID :59868831

Safety of [ 915720-54-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 915720-54-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 915720-54-6 ]

[ 915720-54-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 327056-62-2 ]
  • [ 75-16-1 ]
  • [ 915720-54-6 ]
YieldReaction ConditionsOperation in experiment
95% In tetrahydrofuran; diethyl ether; at -78 - 20℃; for 7.25h;Inert atmosphere; To the solution of 5-fluoropyridine-2-carbonitrile (7.00 g, 57.3 mmol) in tetrahydrofuran (140 mL) cooled to -78 C under argon atmosphere 3 M methylmagnesium bromidesolution in diethyl ether (22.9 mL, 68.8 mmol) was added dropwise during 15 minutes. Reaction mixture was stirred at -78 C for 2 hours, and then at room temperature for 5 hours. A solid precipitated from the reaction mixture. To the reaction mixture 2 M hydrochloric acid solution was added until reaching pH = 6 and dissolution of the precipitate. Then to the mixture 6% sodium hydrogencarbonate solution (100 mL) wasadded. The mixture was extracted with dichloromethane (3 x 150 mL). Organic phases were combined, washed twice with water, brine, dried (Na2504) and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel, eluent:dichloromethane 100% to dichloromethane:acetone, 97:3, v/v) to obtain the product as a light yellow oil with a yield of 95% (7.57 g, 54.4 mmol).
55% a) l-(5-Fluoropyridin-2-yl)ethanone5-Fluoro-pyridine-2-carbonitrile (29 g, 240 mmol) was dissolved in THF (150 mL) under a nitrogen atmosphere. The reaction mixture was cooled to an internal temperature of -64 <n="30"/>C. Methyl magnesium bromide (3M in THF, 105 mL, 315 mmol) was added over 40 min. The reaction mixture was stirred at -65 0C for 1.5 h, then warmed to room temperature. THF (50 mL) was added and the mixture was stirred an additional 3 h. 2M hydrochloric acid (aq., 100 mL) was added until the mixture was slightly acidic and the reaction mixture was stirred at room temperature over night. Sodium bicarbonate was then added to neutralize the reaction mixture. The phases were separated and the aqueous phase was extracted with DCM. The combined organic extracts were washed with Brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography to yield 18 g (55% yield) of the title compound. 1R NMR (300 MHz, CDCl3): 8.50 (m, IH); 8.10 (m, IH); 7.52 (m, IH); 2.70 (s, 3H).
55% a) l-(5-Fluoropyridin-2-yl)ethanone5-Fluoro-pyridine-2-carbonitrile (29 g, 240 mmol) was dissolved in THF (150 mL) under a nitrogen atmosphere. The reaction mixture was cooled to an internal temperature of -64 C. Methyl magnesium bromide (3M in THF, 105 mL, 315 mmol) was added over 40 min. The reaction mixture was stirred at -65 0C for 1.5 h, then it was warmed to room temperature. THF (50 mL) was added and the mixture was stirred an additional 3 h. 2M <n="34"/>hydrochloric acid (aq., 100 mL) was added until the mixture was slightly acidic and the reaction mixture was stirred at room temperature over night. Sodium bicarbonate was then added to neutralize the reaction mixture. The phases were separated and the aqueous phase was extracted with DCM. The combined organic extracts were washed with Brine, dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography to yield 18 g (55% yield) of the title compound. 1H NMR (300 MHz, CDCl3): 8.50 (m, IH); 8.10 (m, IH); 7.52 (m, IH); 2.70 (s, 3H).
54.5% In tetrahydrofuran; at -65 - 20℃; for 4.5h; To a stirred solution of <strong>[327056-62-2]5-fluoropicolinonitrile</strong> (EO, 2.9 g, 23.75 mmol) in THF (20 mL), methylmagnesium bromide (3M in THF, 10.2 mL, 30.87 mmol) was added at -65 C and stirred for 1.5 h. The reaction mixture was further stirred at RT for 3 h. 2M HC1 (10 mL) was added and the reaction mixture was further stirred at RT for 14 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated aqueous NaHC03 solution and extracted with DCM. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 15% EtOAc/hexane to afford compound EP (1.8 g, 54.5%) as a colorless liquid. LC-MS: m/z 140.00 [M+H]+.
34% 10(B) 1 -(5-Fluoro-pyridin-2-yl)-ethanone; To a solution of <strong>[327056-62-2]5-fluoro-pyridine-2-carbonitrile</strong> (2.6 g, 21.31 mmol) in dry THF (50 ml), cooled at - 20C, under nitrogen atmosphere, methylmagnesium bromide (3M solution in diethyl ether, 7.1 ml, 21.31 mmol) was added dropwise. After stirring overnight at - 20C, the reaction mixture was slowly allowed to warm to room temperature, and then a saturated solution of NH4Cl (aq.) was added to adjust the pH to 2. Ethyl acetate was added and the phases were separated. Evaporation of the solvent gave a crude solid that was purified through a silca gel cartridge (eluent: DCM/petroleum ether 1:1). The solid that was recovered from this purification was purified again by flash chromatography (silica gel, eluent: diethyl ether/petroleum ether 1 :9) to afford 1 g of l-(5-fiuoro-pyridin-2-yl)-ethanone. Yield: 34%; LCMS (RT): 3.4 min (Method F); MS (ES+) gave m/z: 140.0 (MH+).

 

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