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

A kind of preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene

A technology of dihydroindene and tetramethyl, applied in the field of organic synthesis, can solve the problems of complicated operation, harsh conditions, low yield and the like

Active Publication Date: 2021-04-27
西安穿越光电科技有限公司
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The invention provides a preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene, which solves the harsh conditions existing in the prior art and the operation Complicated and low-yield technical issues

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 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene
  • A kind of preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene
  • A kind of preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] According to the preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene of the present invention, the method comprises:

[0040] Coupling reaction: use 1 equivalent of o-bromoacetophenone and 1-1.4 equivalents of 9,9-dimethylfluorene-2-boronic acid for coupling reaction to generate the compound shown in formula M-1;

[0041] Wittig reaction: the compound shown in formula M-1 and methyltriphenylphosphonium bromide undergo Wittig reaction to generate the compound shown in formula M-2;

[0042] Cyclization reaction: The compound represented by formula M-2 undergoes a cyclization reaction in the presence of 3 to 16 equivalents of acid, and is converted into 6,6,12,12-tetramethyl-6,12-dihydro represented by formula M Indeno[1,2-b]fluorene;

[0043]

[0044] In the preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene of the present invention, the preparation method includes coupling reaction, Wittig reaction, ring closure re...

Embodiment 1

[0058] The synthetic route is as follows:

[0059]

[0060] According to the preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene of the present invention, the reaction is carried out in three steps:

[0061] (1) Coupling reaction

[0062] 2000 ml there-necked flask, add 19.9 grams (0.1mol, 1eq) o-bromoacetophenone, 26.18 grams (0.11mol, 1.1eq) 9,9-dimethylfluorene-2-boronic acid, 42.4 grams (0.2mol, 2eq) Anhydrous potassium phosphate, 500ml DMF, add 1.06g (0.001mol, 0.01eq) palladium tetrakistriphenylphosphine under the protection of nitrogen, slowly heat to 70-80°C for 8 hours, cool down, add water and toluene to separate the liquid, the water layer Extract once with toluene, combine the organic layers, wash the organic layer with water, wash with saturated brine, dry over anhydrous sodium sulfate, decolorize the silica gel column, concentrate the eluate to dryness, add 300 ml of tetrahydrofuran to obtain tetrahydrofuran containing the compound s...

Embodiment 2

[0070] The synthesis method is the same as in Example 1, except that the amount of 9,9-dimethylfluorene-2-boronic acid used in the first step coupling reaction is changed to 0.12 mol to obtain 23.90 g of the product with a yield of 77.10%.

[0071] The obtained product was carried out 1 HNMR detection, 1 The HNMR spectrum analysis data is as follows: 1 HNMR (500MHz, CDCl 3 ): 8.07 (m, 2H), 7.98 (s, 2H), 7.55 (m, 2H), 7.44 (m, 2H), 7.28 (m, 2H), 1.70 (2, 12H).

[0072] The obtained product was detected by mass spectrometry, and the obtained m / e value was 310.

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 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene. The method comprises: coupling reaction: o-bromoacetophenone and 9,9-dimethylfluorene-2-boronic acid carry out coupling reaction to generate the compound shown in formula M-1; wittig reaction: the compound shown in formula M-1 Carry out addition wittig reaction with methyl triphenylphosphonium bromide, generate the compound shown in formula M-2; Ring closure reaction: carry out ring-closure reaction under the presence of compound acid shown in formula M-2, be converted into the compound shown in formula M 6,6,12,12-Tetramethyl-6,12-dihydroindeno[1,2-b]fluorene. According to the preparation method of the invention, the process is simple and easy to operate; the required raw materials are readily available and the cost is low; and the yield is as high as 66-78%, which is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene. Background technique [0002] 6,6,12,12-Tetramethyl-6,12-dihydroindeno[1,2-b]fluorene is an organic material. 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene can be prepared by bromination reaction to prepare 2,8-dibromo-6,6,12,12- Tetramethyl-6,12-dihydroindeno[1,2-b]fluorene, 2,8-dibromo-6,6,12,12-tetramethyl-6,12-dihydroindeno[1 , The two bromines of 2-b] fluorene are replaced by diarylamine compounds to prepare triarylamine compounds shown in formula (I), which can be used in organic electroluminescent device materials. [0003] [0004] In formula (I), when Ar 1 selected from phenyl, Ar 2 When being selected from 1-naphthyl, its structure is as shown in formula (II), people such as Kimura really disclose the application of triarylamine compound shown in formula (II) as...

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): C07C13/62C07C5/31
CPCC07C1/34C07C5/31C07C45/68C07C13/62C07C13/547C07C49/792
Inventor 李金铃
Owner 西安穿越光电科技有限公司