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Method for preparing 4-chlorine-2H-chromene derivative

A technology for derivatives and chromene, applied in the field of preparation of 4-chloro-2H-chromene derivatives, can solve the problems of reduced yield, increased side reactions, insufficient selectivity, etc., and achieves improved reaction yield and improved operation. The effect of simplicity and high reaction yield

Inactive Publication Date: 2008-07-23
ZHEJIANG UNIV OF TECH
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  • Abstract
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Problems solved by technology

But the used Vilsmeier reagent activity of this method is too strong, selectivity is not good enough, and when reaction temperature is higher than 90 ℃, can cause DMF self to decompose in the reaction, thereby make the side reaction of whole reaction also increase, and yield is reduced greatly

Method used

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  • Method for preparing 4-chlorine-2H-chromene derivative
  • Method for preparing 4-chlorine-2H-chromene derivative
  • Method for preparing 4-chlorine-2H-chromene derivative

Examples

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Effect test

Embodiment 14

[0024] Example 14 Preparation of Chloro-2-phenyl-2H-chromene

[0025] Add 12mL N,N-dimethylformamide and 10mL toluene into a 150mL three-necked reaction flask equipped with magnetic stirring, drying tube, thermometer and dropping funnel, stir and cool to 0-5℃ under ice water bath, then add dropwise Bis(trichloromethyl) carbonate solution (5.94g, dissolved in 15.0mL toluene), react at 0-5℃ for 1 hour after dripping, and then add dropwise containing 1-(2-hydroxyl at 0-5℃ Benzene)-3-phenylchalcone in toluene solution (1.12g, 5mmol, dissolved in 20mL toluene), after dripping, react at 0-5°C for 1 hour, and then heat to 75-85°C for 5 hours. TLC tracks the progress of the reaction. After the reaction, the reaction product was separated and purified: the above reaction mixture was poured into 100g of crushed ice, stirred for 0.5h to complete the hydrolysis, then the organic layer was separated, the aqueous layer was extracted twice with dichloromethane 30mL×2, and the organic layers were...

Embodiment 24

[0027] Example 24-Preparation of chloro-2phenyl-2H-chromene

[0028] Add 2.31mL N,N-dimethylformamide and 5mL toluene into a 150mL three-necked reaction flask equipped with magnetic stirring, drying tube, thermometer and dropping funnel. Stir and cool down to 0-5℃ under ice-water bath, and then drip Add bis(trichloromethyl) carbonate solution (2.97g, dissolved in 5.0mL toluene), after dripping, react at 0-5℃ for 0.5 hours, then add dropwise containing 1-(2- Hydroxybenzene)-3-phenylchalcone in toluene solution (1.12g, 5mmol, dissolved in 12.4mL toluene), after dripping, react at 0-5°C for 0.5 hours, then heat to 75-85°C for reaction 1 hour. Other purification operations were the same as in Example 1, and 0.51 g of 4-chloro-2phenyl-2H-chromene was isolated and the yield was 42%.

Embodiment 34

[0029] Example 34 Preparation of Chloro-2-phenyl-2H-chromene

[0030] Add 2.31mL N,N-dimethylformamide and 8mL toluene into a 150mL three-necked reaction flask equipped with magnetic stirring, drying tube, thermometer and dropping funnel, stir and cool to 0-5℃ under ice water bath, then drop Add bis(trichloromethyl) carbonate solution (2.97g, dissolved in 10.0mL toluene), after dripping, react at 0-5℃ for 0.5 hours, then add dropwise containing 1-(2- Hydroxybenzene)-3-phenylchalcone in toluene solution (1.12g, 5mmol, dissolved in 10.0mL toluene), after dripping, react at 0-5°C for 0.5 hours, and then heat to 75-85°C for reaction 10 hour. Other purification operations were the same as in Example 1, and 0.70 g of 4-chloro-2phenyl-2H-chromene was isolated and the yield was 58%.

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Abstract

The invention discloses a preparation method for 4-Cl-2H-chromene, which is characterized in that: as raw material, bis-(trichloromethyl) carbonate (BTC) and N, N-dimethylformamide (DMF) are reacted fully in organic solvent at the temperature of 0 to 5 DEG C; then substituted o-hydroxy chalcone compound as shown in the formula (I) is added for reaction for 0.5 to 2 hours at the temperature of 0 to 5 DEG C before heated to 60 to 90 DEG C for full reaction; 4-Cl-2H-chromene derivative as shown in the formula (II) can be get through separating and purifying reaction products after the reaction is ended. The preparation method for 4-Cl-2H-chromene has the advantages of easy availability for raw material, mild reaction condition, convenient operation, high yield and chemical synthetic method with better popularization and application prospect. The preparation method for 4-Cl-2H-chromene abolishes phosphate pollution source and greatly lowers the content of N, N-dimethylformamide.

Description

(1) Technical field [0001] The invention relates to a preparation method of 4-chloro-2H-chromene derivatives. (2) Background technology [0002] 4-Chloro-2H-chromene derivatives have certain pharmacological properties and are important intermediates for the synthesis of many natural compounds and pharmaceuticals. At the same time, these compounds also have certain health effects. [0003] 4-Chloro-2H-chromene derivative is a relatively new type of drug intermediate, and there are relatively few reports in the literature. Only an article published by a Japanese scholar in 2005 can find the relevant synthesis method. At that time, a series of substituted o-hydroxy groups were used. Chalcone through POCl 3 / DMF synthesis of Vilsmeier reagent as a catalyst, and DMF as a solvent to synthesize 4-chloro-2H-chromene derivatives at 60-90℃. However, the Vilsmeier reagent used in this method is too active, and the selectivity is not good enough, and when the reaction temperature is higher t...

Claims

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Application Information

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IPC IPC(8): C07D311/04
Inventor 苏为科李振华郑存
Owner ZHEJIANG UNIV OF TECH
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