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Preparation method of 4,4-dihalotetrahydropyran

A technology of tetrahydropyran and dihalogenation, which is applied in 4 fields, can solve the problems of consumption of metal resources, indium trichloride is not enough atomic economy, etc., and achieves the effects of high purity of finished products, reduction of catalytic cost, and reduction of consumption.

Active Publication Date: 2018-04-24
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the synthesis method of the compound is simple and convenient, the use of the chemical equivalent of indium trichloride is not atomically economical and excessive consumption of metal resources

Method used

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  • Preparation method of 4,4-dihalotetrahydropyran
  • Preparation method of 4,4-dihalotetrahydropyran
  • Preparation method of 4,4-dihalotetrahydropyran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation method of 2-phenylethyl-6-phenyl-4,4-dichlorotetrahydro-2H-pyran, the reaction formula is as follows:

[0024]

[0025] The method includes the following steps:

[0026] S1, 0.35 g of 5-chloro-1-phenylhex-5-en-3-ol (1.65 mmol), 0.18 g of benzaldehyde (1.65 mmol), 35 mg of indium trichloride (0.16 mmol) and 10 ml of CH 2 Cl 2 Mix in a flask and stir to form a homogeneous mixture;

[0027] S2. The mixed solution obtained in step S1 is controlled at a temperature of 0° C. by a low-temperature thermostat, and 0.2 g of trimethylchlorosilane (1.82 mmol) is added dropwise to start the reaction;

[0028] S3. Control the temperature of the reaction solution obtained in step S2 at 25-27°C, stir and react for 12 hours, add saturated sodium bicarbonate solution to quench the reaction, move the solution to a separatory funnel, and separate the organic phase and the aqueous phase from the solution ;

[0029] S4, the aqueous phase obtained in step S3 is extracte...

Embodiment 2

[0032] The preparation method of 2-phenethyl-6-phenyl-4,4-dibromotetrahydro-2H-pyran, the reaction formula is as follows:

[0033]

[0034] The method includes the following steps:

[0035] S1, 0.42 g of 5-bromo-1-phenylhex-5-en-3-ol (1.65 mmol), 0.18 g of benzaldehyde (1.65 mmol), 56 mg of indium tribromide (0.16 mmol) and 10 ml of CH 2 Cl 2 Mix in a flask and stir to form a homogeneous mixture;

[0036] S2. The mixed solution obtained in step S1 is controlled at a temperature of 0° C. by a low-temperature thermostat, and 0.28 g of bromotrimethylsilane (1.82 mmol) is added dropwise to start the reaction;

[0037] S3. Control the temperature of the reaction solution obtained in step S2 at 22-25° C., stir and react for 12 hours, add saturated sodium bicarbonate solution to quench the reaction, move the solution to a separatory funnel, and separate the organic phase and the aqueous phase from the solution ;

[0038] S4, the aqueous phase obtained in step S3 is extracted t...

Embodiment 3

[0041]The preparation method of 2-phenethyl-6-phenyl-4,4-diiodotetrahydro-2H-pyran, the reaction formula is as follows:

[0042]

[0043] The method includes the following steps:

[0044] S1, 0.5 g of 5-iodo-1-phenylhex-5-en-3-ol (1.65 mmol), 0.18 g of benzaldehyde (1.65 mmol), 79 mg of indium triiodide (0.16 mmol) and 10 ml of CH 2 Cl 2 Mix in a flask and stir to form a homogeneous mixture;

[0045] S2. The mixed solution obtained in step S1 is controlled at a temperature of 0° C. by a low-temperature thermostat, and 0.36 g of iodotrimethylsilane (1.82 mmol) is added dropwise to start the reaction;

[0046] S3. Control the temperature of the reaction solution obtained in step S2 at 27-30°C, stir and react for 12 hours, add saturated sodium bicarbonate solution to quench the reaction, move the solution to a separatory funnel, and separate the organic phase and the aqueous phase from the solution ;

[0047] S4, the aqueous phase obtained in step S3 is extracted three tim...

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Abstract

The invention relates to a preparation method of 4,4-dihalotetrahydropyran, comprising the steps of mixing halogenated homoallylic alcohol, aldehydes, indium trihalide and a solvent in a flask, mixingwell to obtain a mixed liquid controlled to be -20 to 0 DEG C, dropwise adding trimethyl halogenosilane slowly, starting reaction, allowing reacting by stirring at a certain temperature for 1-24 h, adding sodium bicarbonate saturated solution for quenching reaction, after the solution layers into an organic phase and an aqueous phase, extracting the aqueous phase with methyl tertiary butyl ether,combining the extract to the organic phase, washing the obtained organic phase with saturated salt water, drying, evaporating to remove an organic solvent to obtain a crude product, and subjecting the crude product by separation and purification by column chromatography to obtain a finished product that is applicable to the field of flame retardants and the field of pesticides. The preparation method has simple process and high yield of product, the product has high purity, indium trihalide of catalyst quantity is used in the reaction system, indium consumption is low, the catalyst cost is low, and the preparation method is economical and practical.

Description

technical field [0001] The invention relates to a preparation method of 4,4-dihalogenated tetrahydropyran. Background technique [0002] The same-carbon dihalogenated compound is widely used. It is a main chemical structure of halogen-containing flame retardants and halogen-containing pesticides, especially the same-carbon diiodoalkane, for the reaction of carbon-carbon bond formation catalyzed by many transition metals (such as Simmons-Smith cyclopropanation and Takai-Utimoto olefination) is a valuable synthetic reagent, through which the corresponding compounds such as ketones or aldehydes can also be synthesized. [0003] Li Chaojun reported the preparation of 2,6-disubstituted-4,4-dichlorotetrahydropyran (Li, C.J. et al.Indium-trichloride mediated synthesis of 4 , 4-dichlorotetrahydropyrans. Synlett, 1999, 717-718). Although the synthesis method of the compound is simple and convenient, the use of the chemical equivalent of indium trichloride is not atomically economic...

Claims

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Application Information

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IPC IPC(8): C07D309/08
CPCC07D309/08
Inventor 周海
Owner QUZHOU UNIV
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