Method for synthesizing aromatic formic acid aryl ester derivative

A synthetic method, the technology of aryl boronic acid, applied in the preparation of carboxylic acid halides, organic chemistry, etc., can solve the problems of poor functional group compatibility, reduced yield, low reaction selectivity, etc., and achieve great implementation value and social Economic benefit, good product quality, reaction selectivity and high yield

Inactive Publication Date: 2014-01-08
WENZHOU UNIV
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  • Description
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  • Application Information

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Problems solved by technology

However, this method needs to be carried out under harsh reaction conditions such as high temperature and the use of strong acid as a catalyst, and the reaction yield and functional group compatibility of the substrate are not very good
In addition, the Bayer-Villiger oxidative rearrangement reaction can also be used to synthesize aryl formate derivatives, but the selectivity of this method depends on the difference between the substituents on both sides of the carbonyl group and has high selectivity. However, for aryl formic acid As far as aryl esters are concerned, the substituents on both sides are aryl groups, so they show similar properties, which lead to extremely low reaction selectivity during group migration, which greatly reduces the yield

Method used

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  • Method for synthesizing aromatic formic acid aryl ester derivative
  • Method for synthesizing aromatic formic acid aryl ester derivative
  • Method for synthesizing aromatic formic acid aryl ester derivative

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Experimental program
Comparison scheme
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Embodiment 1

[0031] According to the molar ratio of acid chloride, aryl boronic acid, copper catalyst, ligand, basic compound is 1.0: 1.5: 0.1: 0.2: 2.0 feeding intake; acid chloride is benzoyl chloride, feeding quality 14.1g (0.1mol); aryl boronic acid is Phenylboronic acid, feeding quality 18.3g (0.15mol); copper catalyst is copper acetate, feeding quality 1.82g (0.01mol); ligand is 1,4-diazabicyclo[2.2.2]octane (DABCO), The feeding quality is 2.24g (0.02mol); the basic compound is potassium carbonate, and the feeding quality is 27.6g (0.2mol); the organic solvent is toluene 169g, and its total consumption is 12 times of the quality of benzoyl chloride.

[0032] In an oxygen atmosphere, put benzoyl chloride, phenylboronic acid, copper acetate, 1,4-diazabicyclo[2.2.2]octane (DABCO), and potassium carbonate into the reaction kettle at room temperature, add toluene to dissolve, The reaction temperature was 110°C, and the reaction was completed after 24 hours.

[0033] After the reaction wa...

Embodiment 2

[0036] According to the molar ratio of acid chloride, aryl boronic acid, copper catalyst, ligand, basic compound is 1.0: 1.5: 0.1: 0.2: 2.0 feeding intake; acid chloride is benzoyl chloride, feeding quality 14.1g (0.1mol); aryl boronic acid is Phenylboronic acid, feeding quality 18.3g (0.15mol); copper catalyst is copper acetylacetonate, feeding quality 2.62g (0.01mol); ligand is 1,4-diazabicyclo[2.2.2]octane (DABCO) , feed quality 2.24g (0.02mol); Basic compound is potassium carbonate, feed quality 27.6g (0.2mol); Organic solvent is toluene 169g, and its total consumption is 12 times of benzoyl chloride quality.

[0037] All the other are with embodiment 1, gained product phenyl benzoate 14.5g, yield 73%, purity 98.5%.

Embodiment 3

[0039]According to the molar ratio of acid chloride, aryl boronic acid, copper catalyst, ligand, basic compound is 1.0: 1.5: 0.1: 0.2: 2.0 feeding intake; acid chloride is benzoyl chloride, feeding quality 14.1g (0.1mol); aryl boronic acid is Phenylboronic acid, feeding quality 18.3g (0.15mol); copper catalyst is cuprous acetate, feeding quality 1.23g (0.01mol); ligand is 1,4-diazabicyclo[2.2.2]octane (DABCO) , feed quality 2.24g (0.02mol); Basic compound is potassium carbonate, feed quality 27.6g (0.2mol); Organic solvent is toluene 169g, and its total consumption is 12 times of benzoyl chloride quality.

[0040] All the other are with embodiment 1, gained product phenylbenzoate 12.5g, yield 63%, purity 98.6%.

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Abstract

The invention discloses a method for synthesizing an aromatic formic acid aryl ester derivative shown as a formula (I). The method comprises the following steps of: fully reacting arylboronic acid shown as a formula (II) and acyl chloride shown as a formula (III) which are taken as raw materials in oxygen atmosphere in the presence of a copper catalyst, a ligand and an alkaline compound in an inert organic solvent, and after-treating a reaction solution after the reaction is finished to obtain the aromatic formic acid aryl ester derivative. The method for synthesizing the aromatic formic acid aryl ester derivative is reasonable, low in cost and high in reaction yield, and has relatively high implementation value as well as social and economic benefits; reaction conditions are mild; and the quality of products is high.

Description

(1) Technical field [0001] The invention relates to a chemical synthesis method of aryl formate derivatives. (2) Background technology [0002] Aryl formate derivatives are compounds with good biological and pharmacological activities, and are widely used in the synthesis of organic, pharmaceutical, and pharmaceutical and chemical intermediates. [0003] In the prior art, it is more common to synthesize aryl formate derivatives through the esterification reaction of aromatic formic acid and phenol. However, this method requires harsh reaction conditions such as high temperature and the use of strong acid as a catalyst, and the reaction yield and functional group compatibility of the substrate are not very good. In addition, the Bayer-Villiger oxidative rearrangement reaction can also be used to synthesize aryl formate derivatives, but the selectivity of this method depends on the difference between the substituents on both sides of the carbonyl group and has high selectivit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/78C07C69/92C07C67/14C07D333/38C07D307/68
Inventor 陈久喜吴华悦刘妙昌丁金昌
Owner WENZHOU UNIV
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