Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of preparation method of fluorene compound

A technology of fluorene compounds and compounds, applied in the field of preparation of fluorene compounds, can solve problems such as complex reaction types, harsh reaction conditions in gas phase reactions, and poor compatibility of functional groups

Inactive Publication Date: 2015-07-29
ZHEJIANG SCI-TECH UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, gas-phase reactions are difficult to be used in industrial synthesis due to harsh reaction conditions, complex reaction types, and poor functional group compatibility.

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
  • A kind of preparation method of fluorene compound
  • A kind of preparation method of fluorene compound
  • A kind of preparation method of fluorene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～9

[0079] Preparation of raw materials biphenyltriazene 1b-1i and 1aa: In a 50ml Schlenck tube, add S1 (4.0mmol, 1.0equiv), o-methylphenylboronic acid (4.8mmol, 1.2equiv, CAS: 16419-60-6 ),Pd(PPh 3 ) 4 (0.12mmol, 0.03equiv) and Cs 2 CO 3 (10mmol, 2.5 equiv). Add dioxane / H 2 O (5 / 1, 24ml), and cover the lid immediately after replacing the air with nitrogen. After stirring at 100°C for 12 hours, it was detected that the reaction of the raw materials was complete. After cooling, water (20 mL) was added to quench the reaction, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated NaCl and dried over anhydrous sodium sulfate. The solvent was spun off, and the biphenyltriazenes 1b-1i and 1aa were obtained by passing through the column. The reaction formula is as follows:

[0080]

[0081] The yield of the biphenyltriazene 1b-1i of embodiment 1~9 and 1aa

[0082]

[0083] The structure and characterization da...

Embodiment 10～14

[0103] Preparation of raw materials biphenyltriazene 1j, 1l, 1o, 1s and 1v: In a 50ml Schlenck tube, add triazene phenylboronic acid (4.0mmol, 1.0equiv, CAS: 869670-79-1), o-iodotoluene S2 (4.8mmol, 1.2equiv), Pd (PPh 3 ) 4 (0.12mmol, 0.03equiv) and Cs 2 CO 3 (10mmol, 2.5 equiv). Add solvent dioxane / H 2 O (5 / 1, 24ml), and cover the lid immediately after purging the air with nitrogen. After stirring at 100°C for 12 hours, it was detected that the reaction of the raw materials was complete. After cooling, water (20 mL) was added to quench the reaction, and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with saturated NaCl and dried over anhydrous sodium sulfate. Rotate off the organic solvent, and pass through the column to obtain biphenyltriazene. The reaction formula is as follows:

[0104]

[0105] The yield of the biphenyltriazene 1j, 1l, 1o, 1s and 1v of embodiment 10~14

[0106]

[0107]

[0108]

[0...

Embodiment 15～28

[0119] The preparation of fluorene compound 2: at room temperature, put 1mmol biphenyltriazene in 5mL toluene, add CF dropwise under stirring 3 COOH (CAS: 76-05-1) 456 mg (4 mmol). After stirring for 1 h at 100°C, it was detected that the reaction of the raw materials was complete. Add NaHCO after cooling 3 The reaction was quenched with aqueous solution (10 ml, 0.6 mol / L), and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were washed with saturated NaCl and dried over anhydrous sodium sulfate. The organic solvent was spun off, and the fluorene compound 2 was obtained by passing through the column. The reaction formula is as follows

[0120]

[0121] The yield of the fluorene compound 2 that embodiment 15~28 obtains

[0122]

[0123]

[0124] The characterization data of the product of fluorene compound 2b (CAS: 86-73-7) prepared in Example 15 are as follows:

[0125]

[0126] 2b: white solid; melting point: 106-107°C...

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 preparation method of fluorene compounds. The preparation method comprises the following steps of: carrying out reaction onto biphenyl triazene in a solvent under action of an acid; carrying out simple post-treatment after the reaction is completed to obtain the fluorene compounds. The preparation method disclosed by the invention obtains a series of fluorene compounds through a carbocation-induced sp<3> hydrocarbon bond activating process by adopting triazene biphenyl as a substrate and taking the acid as a catalyst. The preparation method avoids application of a transition metal catalyst, and lowers production cost. Meanwhile, the reaction is carried out in liquid phase, and has important industrial application value.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a preparation method of fluorene compounds. Background technique [0002] Fluorene and its derivatives (referred to as fluorene compounds) are an important class of compounds with a rigid planar biphenyl structure, which contains a large conjugated system in the molecule. This special rigid condensed ring structure makes the fluorene compounds exhibit Many unique optoelectronic properties and biological activities have potential wide applications in optoelectronic materials, medicine and other fields. [0003] In addition, fluorene compounds are also important chemical intermediates, which can be used to prepare medicines (manufacturing antispasmodics, sedatives, analgesics, and hypotensive drugs), dyes (replacing anthraquinone to synthesize indanthrene dyes), synthetic Insecticides and herbicides; making impact-resistant plexiglass and fluorenaldehyde resin...

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
Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/10C07C1/32C07C13/567C07C13/60C07C17/361C07C25/22C07C253/30C07C255/52C07C41/18C07C43/21C07C67/30C07C69/76
Inventor 任红军杨伟君徐丽俊
Owner ZHEJIANG SCI-TECH UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com