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Synthesis method of alpha or beta-substituted aromatic ketone

A synthesis method and technology for aromatic ketones are applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., and can solve the problems of low atom economy, inconvenient operation, and high price of dibutylboron trifluoromethanesulfonate reagent. and other problems, to achieve the effect of high atomic economy, convenient operation and large-scale industrialization.

Active Publication Date: 2021-04-30
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, the dibutyl boron trifluoromethanesulfonate reagent used in the above method is expensive. On the official website of Anaiji: 1970 yuan / 100mL, 1mol / L toluene solution, it brings certain economic benefits to the application of enol boroether synthon pressure
In addition, this method needs to add an equivalent amount of amine, which has low atom economy, and needs to be carried out at low temperature, which is inconvenient to operate

Method used

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  • Synthesis method of alpha or beta-substituted aromatic ketone
  • Synthesis method of alpha or beta-substituted aromatic ketone
  • Synthesis method of alpha or beta-substituted aromatic ketone

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0023] A kind of synthetic method of aromatic ketone substituted in α or β position, specifically as follows:

[0024]

[0025] At room temperature, under nitrogen, in a 10mL Schlenk reaction tube, add PDI-CoCl 2 (0.01mmol), Et 2 O (1 mL), Compound 1a (1 mmol), B 2 pin 2 (1mmol) and NaBHEt 3 (0.02mmol), the reaction solution was stirred at room temperature for 1 hour, compound 2a (1.5mmol) was added, continued to stir at room temperature for 1 hour, and column chromatography separated to obtain compound 3a as a colorless oily liquid with a yield of 92%.

[0026] The NMR characterization data of compound 3a are:

[0027] 1 H NMR (CDCl 3 ,400MHz):δ7.90-7.99(m,2H),7.53-7.63(m,1H),7.41–7.50(m,4H),7.34-7.42(m,2H),7.26-7.35(m,1H) , 5.38 (ddd, J = 6.2, 6.2, 2.4Hz, 1H), 3.65 (d, J = 2.4Hz, 1H), 3.34-3.42 (m, 2H).

Embodiment 2

[0029] Basically the same as embodiment 1, the difference is: adopt LiBHEt 3 instead of NaBHEt 3 , the yield of compound 3a was 85%.

Embodiment 3

[0031] It is basically the same as Example 1, the difference is: adopt THF instead of Et 2 O, the yield of compound 3a was 66%.

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Abstract

The invention discloses a synthesis method of alpha-or beta-substituted aromatic ketone. The method comprises the following steps: under the condition of inert gas, reacting alpha-oxo-aryl ethanone compounds, B2pin2, PDI-CoCl2 and MBHEt3 in an organic solvent at room temperature, then adding a compound 2, and continuously reacting to obtain a compound 3, wherein in the MBHEt3, M is an alkali metal; the compound 2 is selected from the group consisting of deuterated methanol, Selectfluoro, a TogniII reagent or R2CHO; R2 is an aromatic substituent or alkyl; the organic solvent is an aprotic organic solvent. According to the method, the alpha-oxo aryl ethanone is used as a raw material, a cheap and stable boron reagent and an efficient cobalt catalyst which is cheap and easy to obtain are used, an activating reagent MBHEt3 is added to generate an enol boron ether intermediate, then the enol boron ether intermediate and different electrophilic reagents are synthesized into alpha-or beta-substituted aromatic ketone, the reaction is carried out at normal temperature, and the operation is convenient.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a method for synthesizing aromatic ketones substituted at alpha or beta positions. Background technique [0002] Enol boroethers are a class of highly active synthons, which are widely used in synthetic reactions, especially in Aldo condensations. At present, the most commonly used synthesis method of enol boroether is to use ketone and dibutyl boron trifluoromethanesulfonate reagent as raw materials, and to react and synthesize enol boroether under the action of a tertiary amine to obtain enol boroether. The synthetic route is as follows: [0003] [0004] However, the dibutyl boron trifluoromethanesulfonate reagent used in the above method is expensive. On the official website of Anaiji: 1970 yuan / 100mL, 1mol / L toluene solution, it brings certain economic benefits to the application of enol boroether synthon pressure. In addition, this method needs to add an equivalent amount...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C49/82
CPCC07C45/513C07C49/82
Inventor 陈建辉胡海洋夏远志罗燕书温慧婷
Owner WENZHOU UNIVERSITY
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