Unlock instant, AI-driven research and patent intelligence for your innovation.

Preparation method of dibenzo [g, p] condensed dinaphthalene compound

A compound and equation technology, which is applied in the field of preparation of dibenzo[g,p] condensed dinaphthyl compounds, can solve the problems of high raw material manufacturing costs, many reaction intermediates and by-products, and difficulties in the separation and purification of finished products.

Pending Publication Date: 2020-03-13
SHANGHAI CHEMSPEC CORP
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The method needs to prepare a bis-boronate intermediate, which is relatively difficult to prepare and separate, and the cost of raw material manufacturing is relatively high; simultaneously, the efficiency of the ferric chloride system used during the cyclization reaction is low, and the yield can only reach about 50%; the last step even The joint reaction involves multiple reaction sites, the reaction is not easy to reach the end point, and there are many reaction intermediates and by-products, which bring great difficulties to the separation and purification of the finished product

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
  • Preparation method of dibenzo [g, p] condensed dinaphthalene compound
  • Preparation method of dibenzo [g, p] condensed dinaphthalene compound
  • Preparation method of dibenzo [g, p] condensed dinaphthalene compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0060] The present invention provides a method for preparing the compound of formula 1, comprising: subjecting the compound of formula 7 to ring-closing reaction in the presence of an inorganic Lewis acid and an oxidizing agent to prepare the compound of formula 1, and the reaction equation is as follows:

[0061]

[0062] Wherein, R is selected from C1~C5 alkyl;

[0063] R 1 Selected from H, Cl, Br, C1~C5 alkyl, C1~C5 alkoxy, or phenyl;

[0064] R 2 Selected from H, Cl, Br, C1~C5 alkyl, C1~C5 alkoxy, or phenyl;

[0065] R 3 It is selected from H, Cl, Br, C1-C5 alkyl, C1-C5 alkoxy, or phenyl. The inventors of the present invention have provided a new preparation method of dibenzo[g,p] condensed dinaphthyl compound through a large amount of practical research. In the preparation method, an inorganic Lewis acid and an oxidizing agent are used to coordinate an arylation reaction. The compound of formula 7 can undergo ring closure to generate a large conjugated aromatic ri...

Embodiment 1

[0109] Preparation of phenanthrene-9-boronic acid:

[0110] Add 12.5g (0.514mol) metal magnesium and a grain of iodine to a 2000ml four-necked bottle, dissolve 120g (0.467mol) of 9-bromophenanthrene in 600ml THF, add it to a constant pressure dropping funnel, and add 50ml of this mixture dropwise to In the reaction flask, heat to initiate the format, after the initiation, control the temperature between 35°C and 65°C and add the remaining 9-bromophenanthrene solution dropwise, and then reflux and keep warm for 1 hour. Gas chromatography monitors the completion of the reaction of the raw materials. Lower the temperature of the system to -40°C, add dropwise a solution of 63g (0.607mol) trimethyl borate dissolved in 240ml THF, control the temperature to less than -25°C, keep it at this temperature for 1 hour after the dropwise addition, and then naturally rise to room temperature, Add hydrochloric acid dropwise to adjust PH = 1, separate layers, distill off THF under reduced pres...

Embodiment 2

[0113] Preparation of 6-methylphenanthrene-9-boronic acid:

[0114] Add 2.4g (0.100mol) metal magnesium, a grain of iodine, and 10ml MTHF into a 500ml four-necked bottle, dissolve 27.1g (0.100mol) of 6-methyl-9-bromophenanthrene in 27ml MTHF and 108ml toluene, and add constant pressure In the dropping funnel, drop 10ml of this mixture into the reaction bottle, heat to initiate the format, after the initiation, control the temperature between 50°C and 80°C and add the remaining 6-methyl-9-bromophenanthrene solution dropwise, and the dropwise Reflux for another 1 hour. Lower the temperature of the system to -40°C, add 10.9g (0.105mol) trimethyl borate dropwise, control the temperature to less than -25°C, keep warm at this temperature for 1 hour after the dropwise addition, and then naturally rise to room temperature, add hydrochloric acid dropwise to adjust the pH =1, separate layers, evaporate MTHF under reduced pressure, add water for beating, suction filtration, filter cake ...

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 relates to the field of organic synthesis, in particular to a preparation method of a dibenzo [g, p] condensed dinaphthalene compound. The invention provides a preparation method of a compound shown as formula 1. The preparation method comprises the following step: carrying out cyclization reaction on a compound shown as formula 7 in the presence of inorganic Lewis acid and an oxidant to prepare the compound as shown as formula 1. According to the preparation method of the dibenzo [g, p] condensed dinaphthalene compound, the inorganic Lewis acid and the oxidant are adopted for arylation, so that the side reactions generated during the reaction are less, the overall conversion rate of the reaction is high, the raw materials are economical and practical, and the whole reactionroute has characteristics of high reaction yield, convenient industrial production operation, and a good industrialization prospect.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a dibenzo[g,p]condensed dinaphthalene compound. Background technique [0002] Dibenzo[g,p]condensed dinaphthyl compound is an important raw material of a new type of organic light-emitting semiconductor material, and an important raw material capable of self-luminescence in OLEDs. In the existing literature reports, the synthesis route of this type of compound is long, the raw materials are not easy to prepare, and the overall yield is low. Especially in the step of aromatization, the yield is generally not high, the conversion rate is low, the side reactions are complicated, and the purification is difficult, resulting in a higher overall synthesis cost. [0003] There are mainly the following routes to synthesize this type of compound in the existing data: [0004] Route 1 (CN 103649024): [0005] [0006] This method needs to prepare biphenylboron...

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): C07C41/30C07C43/20C07C43/225C07C43/205C07C17/263C07C25/22C07F5/02
CPCC07C41/30C07C17/263C07F5/025C07C2603/54C07C2603/26
Inventor 曾原周彦汪道祥陈晓彬李博蓝袁云龙
Owner SHANGHAI CHEMSPEC CORP