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Preparation method of 1-(tert-butyl)-3-chloronaphthalene

A technology of chloronaphthalene and naphthylamine, which is applied in the field of preparation of 1--3-chloronaphthalene, can solve the problems of many by-products, low yield of target product, complicated process, etc., and achieve less by-products, low cost and environmental friendliness Effect

Active Publication Date: 2022-07-12
JIANGSU NATA OPTO ELECTRONICS MATERIAL
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Problems solved by technology

The existing 1-(tert-butyl)-3-chloronaphthalene synthesis method generally needs at least six process steps, the process is complicated, and the target product yield is also relatively low, and there are many by-products

Method used

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  • Preparation method of 1-(tert-butyl)-3-chloronaphthalene

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preparation example Construction

[0039] Further, a kind of preparation method of 1-(tert-butyl)-3-chloronaphthalene in this typical embodiment comprises the following steps:

[0040] S1. Dissolving 1-naphthylamine in a solvent, adding N-chlorosuccinimide, and extracting after completion of the reaction to obtain intermediate 1 (ie, the aforementioned first intermediate).

[0041] S2. Dissolving intermediate 1 in a solvent, adding N-bromosuccinimide, and extracting after completion of the reaction to obtain intermediate 2 (ie, the aforementioned second intermediate).

[0042] S3. Dissolving intermediate 2 in a solvent, adding Lewis acid and tert-butyl nitrite, and stirring for a certain period of time, adding hypophosphorous acid and cuprous oxide. After completion of the reaction, extraction and column chromatography were performed to obtain Intermediate 3 (ie, the aforementioned third intermediate).

[0043] S4, adding catalyst ligand, nickel acetylacetonate and lithium tert-butoxide into tetrahydrofuran, a...

Embodiment 1

[0046] A preparation method of 1-(tert-butyl)-3-chloronaphthalene comprises the following steps:

[0047] S1. Weigh 1-naphthylamine (about 69.8 mmol), dissolve it in tetrahydrofuran (about 200 mL), slowly add N-chlorosuccinimide (about 69.8 mmol) at 0 °C, and stir at 0 °C for 1 hour. After the reaction was completed, dichloromethane and water were added to the reaction solution, and the layers were extracted and separated. The organic phase was washed twice with saturated sodium carbonate, then washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain Intermediate 1 (about 7.8 g). , the yield is 63%). Characterization results of the intermediate 11HNMR (400MHz, CDCl3): δ=7.83-7.79(m, 2H), 7.54-7.47(m, 2H), 7.54-7.47(m, 2H), 7.38(d, 1H, J = 8.0 Hz), 7.26 (d, 1H, J = 8.0 Hz), 4.58 (brs, 2H).

[0048] S2. Weigh intermediate 1 (about 43.9 mmol), dissolve it in dichloromethane (about 100 mL), add N-bromosuccinimide (about 43.9 mmol) at 0 °C, and...

Embodiment 2

[0052] The preparation method of a kind of 1-(tert-butyl)-3-chloronaphthalene provided by this embodiment comprises the following steps:

[0053] S1, the molar ratio of 1-naphthylamine and N-chlorosuccinimide was adjusted to 1:0.8, the reaction was carried out at 2°C, and the rest were the same as step S1 in Example 1.

[0054] S2. The molar ratio of the first intermediate to the brominating reagent is adjusted to 1:1.2, the brominating reagent is liquid bromine, the reaction is carried out at 2°C, and the rest are the same as in step S2 of Example 1.

[0055] The molar ratio of S3, the second intermediate, Lewis acid, alkyl nitrite, reducing agent, and the first catalyst is adjusted to 1:3:1.2:20:0.05, and the Lewis acid adopts p-toluenesulfonic acid and alkane nitrite. Isoamyl nitrite was used as the base ester, the reaction was carried out at 2°C, and the rest were the same as in step S3 of Example 1.

[0056] S4, the molar ratio of the catalyst ligand, the second catalyst...

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Abstract

The invention discloses a preparation method of 1-(tert-butyl)-3-chloronaphthalene. The preparation method comprises the following steps: reacting 1-naphthylamine with N-chlorosuccinimide in a solvent to generate a first intermediate; reacting the first intermediate with N-bromosuccinimide in a solvent to generate a second intermediate; reacting a first reaction system containing the second intermediate, lewis acid, tert-butyl nitrite and a solvent, and then adding hypophosphorous acid and cuprous oxide into the first reaction system for reaction to generate a third intermediate; and reacting a second reaction system containing a catalyst ligand, nickel acetylacetonate, lithium tert-butoxide, isopropyl magnesium chloride and a solvent in a protective atmosphere, and then adding the third intermediate into the second reaction system for reaction to generate 1-(tert-butyl)-3-chloronaphthalene. The preparation method disclosed by the invention is short in process route, simple to operate, mild in condition, environment-friendly, low in cost, high in target product yield, few in by-products and beneficial to industrial production.

Description

technical field [0001] The application specifically relates to a preparation method of 1-(tert-butyl)-3-chloronaphthalene, which belongs to the technical field of organic chemistry. Background technique [0002] As a new display technology, organic electroluminescent diodes (OLEDs) have the advantages of high brightness, high resolution, wide viewing angle (above 170°), flexibility, fast response, thin thickness, light weight, and low power consumption. . Therefore, the application of OLEDs in flat panel displays, lighting and backlighting has attracted more and more attention. However, the current industrialization process of this technology still faces many key problems, among which the research on OLED molecular materials is the key trend of future research and development. [0003] 1-(tert-butyl)-3-chloronaphthalene is a key intermediate in the synthesis process of OLED molecular materials. The existing 1-(tert-butyl)-3-chloronaphthalene synthesis method generally req...

Claims

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Application Information

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IPC IPC(8): C07C17/263C07C25/22
CPCC07C17/263C07C17/35C07C209/74C07C25/22C07C211/52Y02P20/584
Inventor 成春文郭超李帅丁宗苍朱宇
Owner JIANGSU NATA OPTO ELECTRONICS MATERIAL
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