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

A technology of dihydroindene and 2-b is applied in the preparation of hydroxyl compounds, the preparation of organic compounds, the preparation of carboxylate and other directions, which can solve the problems of harsh conditions, low yield, and complicated operation, and achieve mild reaction conditions and raw materials. Easy-to-obtain, simple-to-craft effects

Active Publication Date: 2018-09-28
烟台新特路新材料科技有限公司
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Problems solved by technology

[0016] 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 problems

Method used

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  • 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

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preparation example Construction

[0040] 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:

[0041] Coupling reaction: use 1 equivalent of methyl o-bromobenzoate and 1 to 1.4 equivalents of 9,9-dimethylfluorene-2-boronic acid for coupling reaction to generate the compound shown in formula M-1;

[0042] Addition reaction: the compound represented by the formula M-1 undergoes an addition reaction with 2 to 3 equivalents of methylmagnesium bromide, followed by hydrolysis to generate the compound represented by the formula M-2;

[0043] 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;

[0044]

[0045] In the preparation method of 6,6,12,12-tetramethyl-6,12-dihydroindeno[1,2-b]fluorene of the present invention, the preparat...

Embodiment 1

[0059] The synthetic route is as follows:

[0060]

[0061] 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:

[0062] (1) Coupling reaction

[0063] 2000 ml there-necked flask, add 21.5 grams (0.1mol, 1eq) methyl o-bromobenzoate, 26.18 grams (0.11mol, 1.1eq) 9,9-dimethylfluorene-2-boronic acid, 42.4 grams (0.2mol, 2eq ) anhydrous potassium phosphate, 500 ml DMF, add 1.06 g (0.001 mol, 0.01 eq) tetrakistriphenylphosphine palladium under nitrogen protection, slowly heat to 70-80 ° C for 8 hours, cool down, add water and toluene to separate liquid, water The layers were extracted once with toluene, the organic layers were combined, the organic layer was washed with water, washed with saturated brine, dried over anhydrous sodium sulfate, passed through a silica gel column, the eluate was concentrated to dryness, and 300 ml of tetrahydrofuran was added to obtain t...

Embodiment 2

[0071] 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 26.61 g of the product with a yield of 85.84%.

[0072] 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).

[0073] The obtained product was detected by mass spectrometry, and the obtained m / e value was 310.

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Abstract

The invention discloses a method for preparing 6, 6, 12, 12-tetramethyl-6, 12-indan [1, 2-beta] fluorene. The method includes carrying out coupling reaction on methyl 2-bromobenzoate and 9, 9-dimethyl fluorene-2-boric acid to generate chemical compounds shown as a formula M-1; carrying out addition reaction on the chemical compounds shown as the formula M-1 and methylmagnesium bromide and hydrolyzing reaction products to generate chemical compounds shown as a formula M-2; carrying out ring-closure reaction on the chemical compounds shown as the formula M-2 in the presence of acid and converting the chemical compounds shown as the formula M-2 into the 6, 6, 12, 12-tetramethyl-6, 12-indan [1, 2-beta] fluorene shown as a formula M. The method has the advantages that processes are simple and are easy to implement; required materials are easily available and are low in cost; the yield can reach 77-88%, and the method 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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/24C07C13/62
CPCC07C1/24C07C29/36C07C67/343C07C69/76C07C33/34C07C13/62
Inventor 李金铃
Owner 烟台新特路新材料科技有限公司
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