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4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene compound and preparation method thereof

A technology for dihydrocyclobutene and naphthalene compounds, applied in chemical instruments and methods, preparation of halogenated hydrocarbons, organic chemistry, etc., can solve the problems of unavailable raw materials and few researches, and achieve low price, simple operation mode, The effect of excellent performance

Active Publication Date: 2015-03-25
MIANYANG DAGAOTE NEW MATERIAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the past, because the raw materials are not easy to obtain, although the performance is excellent, there are few studies on the synthesis of 4-bromo-1,2-dihydrocyclobuteno[α]naphthalene.

Method used

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  • 4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene compound and preparation method thereof
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  • 4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Add 200g of 1,2-dihydrocyclobuteno[α]naphthalene, 1500mL of 90% glacial acetic acid and 150mL of methanol into a 3000mL low-temperature reactor, stir for 2 hours and cool the reaction solution to -5°C; dissolve 200g of bromine In 500ml of 90% glacial acetic acid, bromine solution was obtained. At -5°C, while the reaction solution was stirred, the bromine solution was added dropwise at a constant speed to the reaction solution, and the drop was completed within 4 hours. After the drop, the temperature was continued for 1 hours, to obtain a reddish-brown reaction solution; the obtained reddish-brown reaction solution was transferred to a 3000mL brown bottle, put into a low-temperature freezer, and after reacting for 72 hours at -20°C, the brown bottle was taken out from the low-temperature freezer and placed at room temperature to allow The temperature of the reaction solution reached room temperature. At this time, the reaction solution was a yellow liquid. The obtained y...

Embodiment 2

[0035] Add 300g of 1,2-dihydrocyclobuteno[α]naphthalene, 2500mL of 90% glacial acetic acid and 250mL of methanol into a 5000mL low-temperature reactor, stir for 1 hour and cool the reaction solution to -8°C; dissolve 300g of bromine In 550ml of 90% glacial acetic acid, bromine solution was obtained. At -8°C, while the reaction solution was stirred, the bromine solution was added dropwise at a constant speed to the reaction solution, and the drop was completed within 5 hours. After the drop, the temperature was continued for 2 hours, to obtain a reddish-brown reaction solution; the obtained reddish-brown reaction solution was transferred to a 5000mL brown bottle, put into a low-temperature freezer, and after reacting for 60 hours at -25°C, the brown bottle was taken out from the low-temperature freezer and placed at room temperature to allow The temperature of the reaction solution reached room temperature. At this time, the reaction solution was a yellow liquid. The obtained ye...

Embodiment 3

[0037] Add 300g of 1,2-dihydrocyclobuteno[α]naphthalene, 1700mL of 90% glacial acetic acid and 200mL of methanol into a 5000mL low-temperature reactor, stir for 3 hours and cool the reaction solution to -10°C; dissolve 300g of bromine In 700ml of 90% glacial acetic acid, bromine solution was obtained. At -10°C, while the reaction solution was stirred, the bromine solution was added dropwise at a constant speed to the reaction solution, and the drop was completed within 3 hours. After the drop, the temperature was continued for 3 hours, to obtain a reddish-brown reaction solution; the obtained reddish-brown reaction solution was transferred to a 5000mL brown bottle, put into a low-temperature freezer, and after reacting for 72 hours at -15°C, the brown bottle was taken out from the low-temperature freezer and placed at room temperature to allow The temperature of the reaction solution reached room temperature. At this time, the reaction solution was a yellow liquid. The obtained...

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Abstract

The invention discloses a novel method for synthesizing 4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene. The method comprises the following steps: (1) adding 1,2-dihydrocyclobuteneo[alpha]naphthalene, glacial acetic acid and methanol into a low-temperature reactor, stirring, and reducing the temperature to be 10 DEG C below zero to 0 DEG C; (2) dissolving bromine in glacial acetic acid at the temperature of 10 DEG C below zero to 0 DEG C, dripping reaction liquid, preserving the temperature after the dripping operation of the reaction liquid is finished, keeping the reaction liquid in dark place, putting the reaction liquid in a low-temperature cabinet freezer, reacting at the temperature of 30 DEG C below zero to 15 DEG C below zero, and standing the reaction liquid at room temperature; (3) adding the reaction liquid into dichloromethane, extracting an organic phase, adding an aqueous solution of sodium metabisulfite into the organic phase, stirring, standing, layering, washing by using deionized water, separating out the organic phase, and drying; and (4) concentrating the dried organic phase into thick solid, and recrystallizing, thereby obtaining 4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene. According to the method disclosed by the invention, 1,2-dihydrocyclobuteneo[alpha]naphthalene synthesized by self research and development serves as a raw material, and 4-bromo-1,2-dihydrocyclobuteneo[alpha]naphthalene with excellent performance and low price is synthesized. The reaction conditions are mild, the operation is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to a synthesis method of 4-bromo-1,2-dihydrocyclobuteno[α]naphthalene compound. Background technique [0002] 4-Bromo-1,2-dihydrocyclobuteno[α]naphthalene has important application value and is an important intermediate in organic synthesis. Due to the particularity of the product structure, a series of new Materials with outstanding performance, can replace a variety of imported materials in the pharmaceutical and microelectronics industries, and can be used to make photosensitive materials, charge transport materials, electroluminescent devices, semiconductor bonding, pharmaceutical intermediates, and bioimplantation materials, and therefore in Microelectronics, organic light-emitting semiconductors, micro-electromechanical systems, optical devices, medicine, etc. have broad application prospects. In addition, the compound can greatly reduce production costs un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/12
Inventor 冯毅汪云峰
Owner MIANYANG DAGAOTE NEW MATERIAL
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