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Preparation method of 7-bromine-1-chloronaphthalene

The technology of chloronaphthalene and dihydronaphthalene is applied in the field of preparation of 7-bromo-1-chloronaphthalene, can solve the problems of long steps and high risks, and achieves the effects of short steps, easy handling and good yield

Active Publication Date: 2021-06-18
江苏丽源医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] This route has long steps, requires the use of highly corrosive concentrated sulfuric acid and the dangerous diazotization reaction

Method used

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  • Preparation method of 7-bromine-1-chloronaphthalene
  • Preparation method of 7-bromine-1-chloronaphthalene
  • Preparation method of 7-bromine-1-chloronaphthalene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Chlorination reaction

[0034] In nitrogen atmosphere, 10mmol 7-bromo-3,4-dihydronaphthalene-1(2H)-one (2.25g), 20mmol triphenylphosphine PPh 3 (5.24g) was added to 200mmol CCl 4 (19.3 mL), stirred at room temperature for 30 min, and then heated to reflux to continue the reaction for 5 h. Cool down to room temperature after the reaction, add and CCl 4 An equal amount of n-hexane was diluted, and the precipitated crystals were collected by filtration and washed with n-hexane to obtain 6-bromo-4-chloro-1,2-dihydronaphthalene (yield 75%, 1.83 g, purity 95%).

[0035] aromatization reaction

[0036] In a nitrogen atmosphere, 5mmol 6-bromo-4-chloro-1,2-dihydronaphthalene (1.22g), 15mmol DDQ (3.41g) were added to 100mmol toluene (10.6mL), and reacted at room temperature for 16h. After the reaction was finished, the solid was removed by filtration, and the solid obtained by rotary evaporation was recrystallized from petroleum ether to obtain the final product 7-bromo-1-chl...

Embodiment 2

[0038] Chlorination reaction

[0039] In a nitrogen atmosphere, 10mmol 7-bromo-3,4-dihydronaphthalene-1(2H)-one (2.25g), 20mmol triphenoxyphosphine (6.2g) were added to 200mmol CCl 4 (19.3 mL), stirred at room temperature for 30 min, and then heated to reflux to continue the reaction for 5 h. Cool down to room temperature after the reaction, add and CCl 4 Dilute with an equal amount of n-hexane, collect the precipitated crystals by filtration, and wash with n-hexane to obtain 6-bromo-4-chloro-1,2-dihydronaphthalene (yield 64%, 1.56 g, purity 90%).

[0040] aromatization reaction

[0041] In a nitrogen atmosphere, 5mmol 6-bromo-4-chloro-1,2-dihydronaphthalene (1.22g), 15mmol AIBN (2.46g) were added to 100mmol toluene (10.6mL), and reacted at room temperature for 16h. After the reaction was complete, the solid was removed by filtration. The solid obtained by rotary evaporation of the filtrate was recrystallized from petroleum ether to obtain the final product 7-bromo-1-chlor...

Embodiment 3

[0043] Chlorination reaction is with embodiment 1.

[0044] aromatization reaction

[0045] In a nitrogen atmosphere, 5 mmol 6-bromo-4-chloro-1,2-dihydronaphthalene (1.22 g), 15 mmol TEMPO (2.34 g) were added to 100 mmol toluene (10.6 mL), and reacted at room temperature for 16 h. After the reaction was complete, the solid was removed by filtration. The solid obtained by rotary evaporation of the filtrate was recrystallized from petroleum ether to obtain the final product 7-bromo-1-chloronaphthalene (yield 68%, 0.82 g, purity 89%).

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Abstract

The invention discloses a preparation method of 7-bromine-1-chloronaphthalene, which comprises the following steps of by taking 7-bromine-3, 4-dihydronaphthalene-1 (2H)-ketone as a raw material, mixing the 7-bromine-3, 4-dihydronaphthalene-1 (2H)-ketone, a phosphorus reagent and carbon tetrachloride, and carrying out chlorination reaction to generate 6-bromine-4-chloro-1, 2-dihydronaphthalene, and carrying out aromatization reaction on 6-bromine-4-chloro-1, 2-dihydronaphthalene under the action of an oxidizing agent to generate 7-bromine-1-chloronaphthalene. Compared with a synthesis mode in the prior art, the reaction route has the advantages that the steps are shorter, the adopted reagent is safer and is easy to process, large-scale production is easy to carry out, and the yield is better.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 7-bromo-1-chloronaphthalene. Background technique [0002] 7-Bromo-1-chloronaphthalene is an important organic intermediate used in the fields of medicine and materials. For example, it is not only a key intermediate of new norepinephrine, dopamine, and serotonin reuptake inhibitors (US2006052378 (A1)) but also an intermediate of various new photoelectric materials (CN110981867 (A)). There is basically only one method for the synthesis of 7-bromo-1-chloronaphthalene reported at present, specifically: (1) using 7-bromo-3,4-dihydronaphthalene-1(2H)-one as raw material, and hydrochloric acid Hydroxylamine reacts to generate corresponding oxime; (2) oxime carries out aromatization reaction in the mixed system of concentrated sulfuric acid and acetic anhydride to generate corresponding 7-bromo-1-naphthylamine; (3) 7-bromo-1-naphthylamine undergoes ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/357C07C25/22C07C17/18
CPCC07C17/357C07C17/18C07C25/22
Inventor 杨盟孙璐马圣峰
Owner 江苏丽源医药有限公司
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