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Chemical Structure| 49669-13-8 Chemical Structure| 49669-13-8
Chemical Structure| 49669-13-8

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Product Details of 2-Acetyl-6-bromopyridine

CAS No. :49669-13-8
Formula : C7H6BrNO
M.W : 200.03
SMILES Code : C(C)(=O)C1=NC(=CC=C1)Br
MDL No. :MFCD00272200
InChI Key :RUJTWTUYVOEEFW-UHFFFAOYSA-N
Pubchem ID :11298578

Safety of 2-Acetyl-6-bromopyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Acetyl-6-bromopyridine

* 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 [ 49669-13-8 ]

[ 49669-13-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 49669-13-8 ]
  • [ 75-16-1 ]
  • [ 638218-78-7 ]
YieldReaction ConditionsOperation in experiment
98% Preparation 31 Synthesis of 2-(6-bromo-pyridin-2-yl)-propan-2-ol Add a solution of methyl magnesium bromide (3.0 M, 9.7 mL, 29.09 mmol) in tetrahydrofuran dropwise over 20 min to a cooled solution of 1-(6-bromo-pyridin-2-yl)-ethanone (5 g, 24.25 mmol) in anhydrous tetrahydrofuran (48.5 mL) at 0 C. Upon completion of the reaction, add water (exothermic), dilute with ethyl acetate (50 mL) and separate the layers. Extract the aqueous layer once with ethyl acetate (50 mL). Dry the combined organic layers over sodium sulfate, filter and concentrate to give the title compound as a pale yellow liquid (5.69 g, 98%) that is used without further purification. 1H NMR (CDCl3) delta 1.55 (s, 6H), 4.07 (s, 1H), 6.59 (t, 1H), 7.37 (t, 2H), 7.55 (t, 1H).
98% In tetrahydrofuran; at 20℃; for 16h; To a solution of l-(6-bromo-pyridin-2-yl)-ethanone (4.0 g, 20 mmol) in anhydrous THF (50 mL) at 0 C was added a solution of methyl magnesium bromide (3.0 M, 8.0 mL, 24 mmol, 1.2 eq) in THF dropwise over 20 min. The mixture was stirred at rt for 16 h, quenched with H20 (30 mL) and extracted by EA (4 x 30 mL). The organic phase was washed with brine (30 mL) and dried over Na2S04. After filtration and concentration, the residue was directly used for next step without further purification. 4.2 g, Y: 98%. ESI-MS (M+H)+: 216.
A solution of l-(6~bromorhoyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 ml) at 00C was treated with methyl magnesium bromide (8.33 ml, 25.0 mmol). After 3 hours, water was added to quench excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound. LRMS (APCI) calc'd for C8H1 jBrNO [M+H]+: 216, Found: 216.
In diethyl ether; at 0℃; for 3h; A solution of l-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 mL) at 0C was treated with methyl magnesium bromide (8.33 mL, 25.0 mmol). After 3 hours, water was added to quench the excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound.Calc'd for C8HnBrNO [M+H]+: 216, Found: 216.

  • 2
  • [ 49669-13-8 ]
  • [ 325142-82-3 ]
  • [ 1227055-11-9 ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 16h;Reflux; Inert atmosphere; The colorless oily liquid of Preparation 1 (0.68 g, 2.5 mmol), 6-acetyl-2-bromopyridine (0.50 g, 2.5 mmol) and tetrakis(triphenylphosphine)palladium(Pd(PPh3)4, 144 mg, 0.13 mmol) were added in a 100 ml single neck bottle followed by adding THF (25 ml) and a potassium carbonate solution (potassium carbonate (0.69 g) in deionized water (5 ml)) to obtain a mixture. The mixture was heated under reflux for 16 hours under a nitrogen gas atmosphere. After the reaction was finished, the mixture was cooled to room temperature, followed by removing solvent by virtue of reduced pressure distillation to obtain a distilled mixture. Then, the distilled mixture was added with dichloromethane and water for extraction. The dichloromethane layer was collected and added with magnesium sulfate to remove water. The dichloromethane layer was then filtrated and the filtrate was collected. Next, the filtrate was concentrated by means of reduced pressure distillation to obtain a yellow crude product. The resultant yellow crude product was subjected to column chromatography, in which a mixture of ethyl acetate and hexane(ethyl acetate: hexane=1:8) was used as an eluent. An eluate was collected followed by removing the eluent using a rotary evaporator. A white solid product was obtained (446 mg, 1.7 mmol, 67% yield). The spectrum analysis for the white solid product is: 1H NMR (400 MHz, CDCl3, 298K), delta(ppm): 8.34 (s, 1H), 8.27 (d, JHH=8.0 Hz, 1H), 8.02 (dd, JHH=6.8 Hz, 2.0 Hz, 1H), 7.98?7.90 (m, 2H), 7.70 (d, JHH=8.0 Hz, 1H), 7.63 (t, JHH=8.0 Hz, 1H), 2.82 (s, 3H).
  • 3
  • [ 49669-13-8 ]
  • [ 7072-01-7 ]
  • C40H28Br4N6 [ No CAS ]
 

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