Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of 1-bromo-9,9'-spirodifluorene

A synthesis method, the technology of spirobifluorene, applied in the field of organic chemical synthesis, can solve the problems of 1-bromofluorenone, which is expensive, difficult to industrialize production, and affects the potential application of luminescent materials, etc., and achieves improved solubility, reduced cost, and low cost Effect

Active Publication Date: 2016-07-06
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-Bromo-9,9'-spirobifluorene is highly modifiable and has become a research hotspot in recent years. However, 1-bromofluorenone is usually used as the starting material at present. 1-Bromofluorenone is expensive and difficult to industrialize. production, and thus affect its potential application in luminescent materials, there is an urgent need to develop new methods suitable for industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 1-bromo-9,9'-spirodifluorene
  • Synthesis method of 1-bromo-9,9'-spirodifluorene
  • Synthesis method of 1-bromo-9,9'-spirodifluorene

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022]

[0023] Under argon protection, 6.0 g (0.25 mol) of magnesium powder was added to a 500 mL three-neck flask, and immersed in 30 mL of methyltetrahydrofuran (dry) solution. Under stirring, add about 5mL of 1,3-dibromobenzene in methyl tetrahydrofuran dropwise to the above reaction solution, after the Grignard reagent triggers, slowly drop in the remaining 1,3-dibromobenzene in methyl tetrahydrofuran solution 100mL , add a total of 47.2g (0.2mol) 1,3-dibromobenzene, after dripping, reflux for 6h to synthesize 3-bromophenylmagnesium bromide; then under the protection of argon, first add 4.5g (0.02mol) of zinc bromide, Then add 100mL o-xylene solution containing 65.8g (0.2mol) of 1,2-diiodobenzene and 4.8g (0.2mol) of magnesium powder to the above reaction solution, control the reaction temperature at 90°C, and reflux for 10h to form 3-Bromobiphenyl magnesium iodide. Under the protection of argon, add 36 g (0.2 mol) of fluorenone in methyl tetrahydrofuran solution drop...

example 2

[0027]

[0028] Under argon protection, 18.0 g (0.75 mol) of magnesium powder was added to a 1 L three-necked flask, and immersed in 100 mL of methyl tetrahydrofuran (dry) solution. Under stirring, add about 5mL of 1,3-dibromobenzene in methyl tetrahydrofuran dropwise to the above reaction solution, after the Grignard reagent triggers, slowly drop in the remaining 1,3-dibromobenzene in methyl tetrahydrofuran solution 200mL , add 165.2g (0.7mol) 1,3-dibromobenzene in total, after dropping, reflux for 7h to synthesize 3-bromophenylmagnesium bromide; then under the protection of argon, first add 7.12g (0.032mol) 300mL of o-xylene solution containing 188.1g (0.665mol) of o-bromoiodobenzene was dropped into the above reaction solution, the reaction temperature was controlled at 120°C, and the reaction was refluxed for 12 hours to generate 3-bromobiphenylmagnesium bromide. Under the protection of argon, add 113.5 g (0.63 mol) of fluorenone in methyl tetrahydrofuran solution dropw...

example 3

[0030]

[0031]Under the protection of argon, put 10.8g (0.45mol) of magnesium powder into a 1L three-necked flask, and immerse it with 100mL of methyltetrahydrofuran (dry) solution. Under stirring, add about 5mL of 1,3-dibromobenzene in methyl tetrahydrofuran dropwise to the above reaction solution, after the Grignard reagent triggers, slowly drop in the remaining 1,3-dibromobenzene in methyl tetrahydrofuran 300mL , a total of 94.4g (0.4mol) of 1,3-dibromobenzene was added, after dropping, refluxed for 6h to synthesize 3-bromophenylmagnesium bromide; then under the protection of argon, 19.8g (0.088mol) of zinc bromide was first added, Then 200mL of o-xylene solution containing 104.9g (0.44mol) of o-chloroiodobenzene was dropped into the above reaction solution, the reaction temperature was controlled at 140°C, and the reaction was refluxed for 8 hours to generate 3-bromobiphenylmagnesium chloride. Under the protection of argon, add 72g (0.4mol) of fluorenone in methyl tetr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method of 1-bromo-9,9'-spirodifluorene, belonging to the field of organic chemical synthesis. The method comprises the following steps: in an inert gas protective atmosphere, preparing a Grignard reagent in a methyl tetrahydrofuran solvent by using 1,3-dibromobenzene as an initial raw material, continuing reacting with ortho-halogen iodobenzene and magnesium powder under the catalytic action of zinc bromide, carrying out reaction with fluorenone, carrying out hydrolysis, and carrying out intramolecular closed loop synthesis under the catalytic action of boron trifluoride to obtain the 1-bromo-9,9'-spirodifluorene. The synthesis method has the advantages of simple process and cheap and accessible raw material, obviously lowers the production cost of the product, and widens applicability of fluorene derivatives as an intermediate in organic photoelectric material design and synthesis.

Description

technical field [0001] The invention relates to a synthesis method of fluorene derivatives, in particular to a synthesis method of 1-bromo-9,9'-spirobifluorene, which belongs to the field of organic chemical synthesis. Background technique [0002] Organic electroluminescent materials have the advantages of wide material selection, low energy consumption, high efficiency and luminous brightness, ultra-thin, full curing, fast response, active light emission, and large-area flexible display, etc., and are expected to become the new generation of flat panel display technology. The core component has become one of the research hotspots in the fields of organic electronics and optoelectronic information. Fluorene has high photothermal stability, the solid-state fluorene fluorescence quantum efficiency is as high as 60%-80%, and the band gap energy is greater than 2.90eV. Fluorene has a certain modifiability in structure, but the rigid planar biphenyl unit of fluorene makes it ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C17/35C07C25/22
CPCC07C17/35C07C29/64C07F3/02C07C25/22C07C35/52
Inventor 杨振强王朝杰李奎杨瑞娜陈鹏丽周铎
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com