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

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

Inactive Publication Date: 2007-11-14
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 After 6 to 8 hours, follow-up detection by TLC (ethyl acetate:n-hexane:acetic acid=10:20:1 as developing solvent). 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-acetyl) 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 (aceti...

Embodiment 2

[0058] (1) Preparation of trans-(4-acetyl) 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 developing solvent). 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-acetyl)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-acetyl)cinnamic acid (III)...

Embodiment 3

[0071] (1) Preparation of trans-(4-acetyl) 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 developing solvent). 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, 1.0 g of trans-(4-acetyl)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-acetyl) cinnamic acid (III),...

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Abstract

This invention belongs to functional macromolecule technosphere, concretely relates to preparation method of a antiform-4-( beta- bromethylene group) phenoxy benzyl type resin(1). The invention adopts antiform-4-( beta- bromethylene group) benzoic acid and Wang resin as raw material, under tetrahydrofuran,triphenyl fosforus, azo dimethoxy diethylmaleate system, at room temperature synthesize antiform and cis form- 4-( beta- bromethylene group) benzoyl oxygen benzyl type resin that contain bromethylene active group. This product could be used as initial raw material of many kinds of compound chemical synthesis, useful for medicine, pesticide, natural product with biological activity, liquid crystal, functional stuff 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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IPC IPC(8): C08F8/18C08F12/08C08K5/02
Inventor 匡春香江玉波
Owner CHIZHOU DONGSHENG PHARMA