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Preparation method of arylpropylaldehyde derivatives

A technology for aryl propionaldehyde and derivatives, which is applied in the field of preparation of aryl propionaldehyde derivatives, can solve the problems of harsh reaction conditions, high production equipment requirements, and poor operability, and achieve easy industrial production and low production equipment requirements , the effect of mild reaction conditions

Inactive Publication Date: 2013-09-04
中国中化股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the need to use the precious metal palladium and the production of isomers, the method is limited in application
[0012] Looking at the preparation methods of aryl propionaldehyde derivatives that have been disclosed, the sources of raw materials are difficult and expensive, and multiple oxidation and reduction reactions are required, the route is lengthy, the reaction conditions are harsh, the operability is poor, the requirements for production equipment are high, and the pressure on safety and environmental protection is high. , difficult product purification, low yield, unfavorable for industrial production

Method used

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  • Preparation method of arylpropylaldehyde derivatives
  • Preparation method of arylpropylaldehyde derivatives
  • Preparation method of arylpropylaldehyde derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of m-trifluoromethyl phenylpropanal

[0045] Preparation of m-trifluoromethylphenylboronic acid

[0046] Under nitrogen, m-trifluoromethylbromobenzene (2.3 g, 0.01 mol), magnesium (2.7 g, 0.11 mol), 10 mL of ether and 50 mg of iodine were added to a flask equipped with a stirrer, condenser, and thermometer, The color of iodine induced by heating disappeared. Then m-trifluoromethylbromobenzene (23 g, 0.1 mol) and 60 ml of diethyl ether were dropped into the flask at 30° C., keeping a slight boil. After dropping, the mixture was stirred and reacted at reflux for 2 hours. After the reaction, cool to room temperature, add trimethyl borate (114.6 g, 1.1 mol) cooled to -78°C and 20 ml of diethyl ether, and stir for 12 hours. Warming up to room temperature, pouring into 1 mol / L hydrochloric acid aqueous solution for acid hydrolysis. After the acid hydrolysis was completed, 100 ml of ethyl acetate was added to extract and separate the organic l...

Embodiment 2

[0049] Embodiment 2: the preparation of p-tert-butylphenylpropionaldehyde

[0050] Preparation of p-tert-butylphenylboronic acid

[0051] Under nitrogen, add p-tert-butylbromobenzene (2.1 g, 0.01 mol), magnesium (2.9 g, 0.12 mol), 10 mL THF and 50 mg iodine to a flask equipped with a stirrer, condenser and thermometer, and heat cause. Then, p-tert-butylbromobenzene (21.3 g, 0.1 mol) and 60 ml of tetrahydrofuran were dropped into the flask at 40° C., keeping slight boiling. After dropping, reflux and stir the reaction for 1 hour. After the reaction, cool to room temperature, and add tributyl borate (24.4 g, 0.12 mol) and 30 ml tetrahydrofuran cooled to -78°C. The reaction was stirred for 12 hours. Warming up to room temperature, pouring into 1 mol / L sulfuric acid aqueous solution for acid hydrolysis. After the acid hydrolysis was completed, 100 ml of ethyl acetate was added, the organic layer was separated, and the aqueous layer was extracted twice with 100 ml of ethyl ace...

Embodiment 3

[0054] Embodiment 3: the preparation of phenylpropionaldehyde

[0055] Preparation of phenylboronic acid

[0056] Under nitrogen, bromobenzene (1.6 g, 0.01 mol), magnesium (3.2 g, 0.13 mol), 10 ml of tetrahydrofuran and 50 mg of iodine were added to a flask equipped with a stirrer, condenser and thermometer, and heated to initiate. Then bromobenzene (15.7 g, 0.1 mol) and 60 ml of tetrahydrofuran were dropped into the flask at 40° C., keeping a slight boil. After dropping, the reaction was stirred at 25°C for 3 hours. After completion of the reaction, cool to room temperature, add tributyl borate (24.4 g, 0.12 mol) cooled to -78°C and 30 ml THF, and stir for 72 hours. Warming up to room temperature, pouring into 1 mol / L sulfuric acid aqueous solution for acid hydrolysis. After the acid hydrolysis was completed, 100 ml of ethyl acetate was added, the organic layer was separated, and the aqueous layer was extracted twice with 100 ml of ethyl acetate. The organic layers were c...

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Abstract

The invention relates to a preparation method of arylpropylaldehyde derivatives. The method contains the arylpropylaldehyde derivatives which are shown in the formula I and prepared according to the route shown as below, wherein R1, R2, R3, R4 and R5 represent hydrogen, C1-4 alkyl, C1-4 alkoxy, fluorine, chloride, trihalogenated methyl or nitryl independently and respectively; R6 represents hydrogen or C1-4 alkyl; and X represents fluorine, chlorine, bromine or iodine. The method has common and cheap raw material, simple route, mild reaction conditions, low requirements on the production equipment and low discharge amount, does not adopt oxidation and reduction reactions and conforms to the current trend of green chemistry; and the arylpropylaldehyde derivatives are synthetized, high yield and purity can be realized and the industrialized production is easy to realize, thus the preparation method can be widely used to synthetize medicines, daily chemical products and the like.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular, the invention relates to a preparation method of aryl propionaldehyde derivatives. Background technique [0002] Aryl propionaldehyde derivatives (formula I) are an important class of compounds, which play a very important role in the construction of aryl propyl synthons. For example wherein a kind of specific compound m-trifluoromethylphenylpropionaldehyde (formula a) is exactly the key intermediate of synthetic new drug Sensipar (cinacalcet, cinacalcet, formula b) (see for example US 6211244; Drugs 2002, 27 (9 ), pp. 831-836). The new drug Sensipar is a new drug approved by the FDA for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis and hypercalcemia in patients with parathyroid cancer. The first drug in a new class of compounds called calcimimetics. The drug activates calcium receptors in the parathyroid glands, thereby reduc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/68C07C47/24C07C47/228C07C47/277
Inventor 陈维翁科杰宋文芳杨建军
Owner 中国中化股份有限公司
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