Alkyl and aryl ketone compound preparation method

A technology for alkyl aryl ketones and compounds, which is applied in the field of organic chemical synthesis, can solve the problems of expensive catalyst and low yield, and achieves the effects of simple operation, high yield and increased reaction activity

Inactive Publication Date: 2013-09-04
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] In view of this, in order to solve many defects such as low yield, expensive catalyst, etc. that exist in the above-mentioned prior art, the present inventor is for aliphatic nitr

Method used

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  • Alkyl and aryl ketone compound preparation method
  • Alkyl and aryl ketone compound preparation method
  • Alkyl and aryl ketone compound preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the synthesis of methyl phenyl ketone

[0062]

[0063] In a reaction vessel equipped with a stirrer, a thermometer, and a feeding port, add 25ml of tetrahydrofuran, 10mmol of acetonitrile, 10mmol of potassium phenyltrifluoroborate, 0.2mmol of palladium trifluoroacetate, 0.2mmol of 2,2'-bipyridine and 50mmol of trifluoroacetic acid , replaced by nitrogen three times, and then stirred and reacted at 60° C. for 15 hours under the protection of continuous feeding of nitrogen. After the reaction was completed, it was left to cool down to room temperature; the organic layer was separated and extracted with saturated sodium bicarbonate and saturated saline, and evaporated to dryness to obtain the target product with a yield of 98% and a purity of 98.2% (HPLC).

[0064] NMR: 1 H NMR (CDCl 3 , 500MHz) δ7.96(d, J=7.1Hz, 2H), 7.57(t, J=7.4Hz, 1H), 7.47(t, J=7.4Hz, 2H), 2.61(s, 3H);

[0065] 13 C NMR (CDCl 3 , 125MHz) δ198.2, 137.2, 133.1, 128.6, 128.3, 26.6....

Embodiment 2

[0066] Embodiment 2: the synthesis of methyl phenyl ketone

[0067]

[0068] In a reaction vessel equipped with a stirrer, a thermometer, and a feeding port, add 20ml of toluene, 10mmol of acetonitrile, 20mmol of sodium phenyltrifluoroborate, 0.5mmol of palladium trifluoroacetate, and 1mmol of 3,3'-dimethyl-2,2' -Bipyridine and 100 mmol trifluoroacetic acid, replaced with nitrogen three times, and then stirred and reacted at 80° C. for 20 hours under the protection of continuous feeding of nitrogen. After the reaction was completed, it was left to cool down to room temperature; the organic layer was separated and extracted with saturated sodium bicarbonate and saturated saline, and evaporated to dryness to obtain the target product with a yield of 91% and a purity of 99.4% (HPLC).

[0069] NMR: 1 H NMR (CDCl 3 , 500MHz) δ7.96(d, J=7.1Hz, 2H), 7.57(t, J=7.4Hz, 1H), 7.47(t, J=7.4Hz, 2H), 2.61(s, 3H);

[0070] 13 C NMR (CDCl 3 , 125MHz) δ198.2, 137.2, 133.1, 128.6, 128.3,...

Embodiment 3

[0071] Embodiment 3: the synthesis of cuminone

[0072]

[0073] In a reaction vessel equipped with a stirrer, a thermometer, and a feeding port, add 35 ml of dichloromethane, 15 mmol of isobutyronitrile, 45 mmol of potassium phenyltrifluoroborate, 1.5 mmol of palladium trifluoroacetate, 3 mmol of 4,4'-bipyridine and 120 mmol of Trifluoroacetic acid was replaced with nitrogen three times, and then stirred and reacted at 100° C. for 24 hours under the protection of continuous feeding of nitrogen. After the reaction was completed, it was left to cool down to room temperature; the organic layer was separated and extracted with saturated sodium bicarbonate and saturated brine respectively, and the target product was obtained after rotary evaporation to dryness, with a yield of 94% and a purity of 98.9% (HPLC).

[0074] NMR: 1 H NMR (CDCl 3 , 500MHz) δ7.95(d, J=7.7Hz, 2H), 7.55(t, J=7.3Hz, 1H), 7.46(t, J=7.7Hz, 2H), 3.60-3.56(m, 1H), 1.22(d, J=6.9Hz, 6H);

[0075] 13 C NMR ...

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Abstract

The invention relates to an alkyl and aryl ketone compound synthetic method. The method comprises a step of enabling an aliphatic nitrile compound to react with aryl sodium trifluoroborate in an organic solvent in the presence of a palladium catalyst, dipyridyl and trifluoroacetic acid so as to prepare the target product through one step. The method has the advantages of high product yield, convenience in operation, simple method and the like; and the method has a good scientific research value and an industrial application prospect.

Description

technical field [0001] The invention relates to a synthesis method of a carbonyl compound, in particular to a synthesis method of an alkyl aryl ketone compound, and belongs to the field of organic chemical synthesis. Background technique [0002] Ketones have always been a widely used compound, which can be applied in the field of organic synthesis of various compounds. Due to the presence of carbonyl, it endows it with good reactivity. Therefore, ketones have been used for a long time. It has gained wide attention and is widely used in many fields. [0003] For the synthesis of ketone compounds, various chemical synthesis methods and routes have been developed. In recent years, the addition reaction of nitriles and organoboron reagents under the catalysis of transition metals to obtain ketones has become an important method for the synthesis of ketones. People have conducted in-depth research on this. A large number of different ketone compounds were synthesized by the ch...

Claims

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Application Information

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IPC IPC(8): C07C49/76C07C49/84C07C49/807C07C45/00
Inventor 吴华悦陈久喜刘妙昌黄小波高文霞
Owner WENZHOU UNIVERSITY
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