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Method for preparing trans-4-(beta-bromoethyl) phenoxy-benzylic resin (I)

A technology of phenoxybenzyl type and vinyl bromide, which is applied in the field of preparation of trans-4-phenoxybenzyl type resin, and achieves the effect of great application prospects

Inactive Publication Date: 2009-08-05
CHIZHOU DONGSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] About the preparation method of trans-4-(beta-bromovinyl) phenoxy benzyl resin, there is no report in domestic and foreign literature

Method used

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  • Method for preparing trans-4-(beta-bromoethyl) phenoxy-benzylic resin (I)
  • Method for preparing trans-4-(beta-bromoethyl) phenoxy-benzylic resin (I)
  • Method for preparing trans-4-(beta-bromoethyl) phenoxy-benzylic resin (I)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Preparation of 4-hydroxycinnamic acid (II)

[0039]

[0040] In a 50mL flask equipped with a reflux condenser and a thermometer, add 0.611g (5mmol) of 4-hydroxybenzaldehyde, 1.040g (10mmol) of malonic acid, 10mL of pyridine, and 0.01mL of piperidine, raise the temperature to 80°C, and stir the reaction 6 to 8 hours, followed by TLC detection (ethyl acetate: n-hexane: acetic acid = 10:20:1 as developer). After the reaction, cool to room temperature, neutralize with 6M cold hydrochloric acid to pH = 2, filter, wash with ice water and ethyl acetate, P 2 o 5 Vacuum drying gave 0.700 g of light yellow powder, namely 4-hydroxycinnamic acid (II), with a yield of 92%.

[0041] (2) Preparation of trans-(4-acetoxy) cinnamic acid (III)

[0042]

[0043] In a 25mL flask equipped with a calcium chloride drying tube, add 0.761g (5mmol) 4-hydroxycinnamic acid (II), 5mL acetic anhydride, 0.5mL triethylamine, react at 70°C for 2 hours, TLC tracking detection (acetic acid Eth...

Embodiment 2

[0058] (1) Preparation of trans-(4-acetoxy) cinnamic acid (III)

[0059]

[0060] In a 25mL flask equipped with a calcium chloride drying tube, add 0.761g (5mmol) of commercially available 4-hydroxycinnamic acid (II), 5mL of acetic anhydride, and 0.7mL of triethylamine, and react at 80°C for 3 hours, followed by TLC Detection (ethyl acetate: n-hexane: acetic acid=10:20:1 as developer). After the reaction, add 15 mL of water, and stir vigorously at room temperature for 0.5 hour to completely decompose the acetic anhydride and the system becomes cloudy. Filtered, the filter cake was washed 3 times with 20mL water, washed with P 2 o 5 After vacuum drying, 0.979 g of trans-(4-acetoxy)cinnamic acid (III) was obtained, with a yield of 95%.

[0061] (2) Preparation of trans-4-(β-bromovinyl)phenyl acetate (IV)

[0062]

[0063] To 10 mL of reaction medium (9.0 mL of acetonitrile and 1.0 mL of water) was added 1.031 g (5.0 mmol) of trans-(4-acetoxy)cinnamic acid (III), 0.934 ...

Embodiment 3

[0071] (1) Preparation of trans-(4-acetoxy) cinnamic acid (III)

[0072]

[0073] In a 25mL flask equipped with a calcium chloride drying tube, add 0.761g (5mmol) of commercially available 4-hydroxycinnamic acid (II), 8mL of acetic anhydride, and 0.7mL of triethylamine, and react at 60°C for 2 hours, followed by TLC Detection (ethyl acetate: n-hexane: acetic acid=10:20:1 as developer). After the reaction was completed, 15 mL of water was added, and vigorously stirred at room temperature for 0.5 hour, so that the acetic anhydride was completely decomposed and the system became cloudy. Filtered, the filter cake was washed 3 times with 20mL water, washed with P 2 o 5 After vacuum drying, 1.0 g of trans-(4-acetoxy)cinnamic acid (III) was obtained with a yield of 97%.

[0074] (2) Preparation of trans-4-(β-bromovinyl)phenyl acetate (IV)

[0075]

[0076] In 10 mL of reaction medium (9.5 mL of acetonitrile and 0.5 mL of water) were added 1.031 g (5.0 mmol) of trans-(4-acet...

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Abstract

The invention belongs to the technical field of functional macromolecules, and in particular relates to a preparation method for synthesizing trans-4-(β-bromovinyl)phenoxy benzyl resin (I). The present invention adopts trans-4-(β- Bromovinyl) phenol and Wang resin were used as raw materials, and trans-4-(β-bromoethylene containing bromoethylene active groups was synthesized at room temperature in tetrahydrofuran, triphenylphosphine, and diethyl azodicarboxylate system. base) phenoxy benzyl resin. The trans-4-(beta-bromovinyl) phenoxy benzyl resin synthesized by this method takes vinyl bromide as a reactive group, and can be used as a starting material for the combinatorial chemical synthesis of many types of compounds for use in medicines, pesticides, Synthesis of physiologically active natural products, liquid crystals, functional materials, etc.

Description

technical field [0001] The invention belongs to the technical field of functional polymer materials, and in particular relates to a preparation method of trans-4-(β-bromovinyl)phenoxy benzyl resin (I). technical background [0002] Synthesis of substituted alkenes with high stereoselectivity has always been one of the most important focuses in organic synthesis. When synthesizing physiologically active unsaturated natural products or drugs, generally only one isomer is physiologically active, so stereochemical control is Very important and meaningful, the carbon-carbon double bond with cis or trans configuration is also an important structural unit of functional polymer materials and optical linear materials. [0003] In recent years, with the increasing demand for compounds for drug screening, the development of synthetic techniques is urgently required to meet the need to provide a large number of organic compounds. Combinatorial chemistry is a new type of synthesis techn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F8/18C08F12/08C08K5/02
Inventor 匡春香江玉波
Owner CHIZHOU DONGSHENG PHARMA
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