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A kind of preparation method of 7-bromo-1-chloronaphthalene

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

Active Publication Date: 2022-06-14
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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  • A kind of preparation method of 7-bromo-1-chloronaphthalene
  • A kind of preparation method of 7-bromo-1-chloronaphthalene
  • A kind of preparation method of 7-bromo-1-chloronaphthalene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Chlorination

[0034] Under a nitrogen atmosphere, 10 mmol of 7-bromo-3,4-dihydronaphthalene-1(2H)-one (2.25 g), 20 mmol of triphenylphosphine PPh 3 (5.24g) added to 200mmol CCl 4 (19.3 mL), stirred at room temperature for 30 min, then heated to reflux and continued the reaction for 5 h. After the reaction, it was lowered to room temperature, and CCl was added. 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 (75% yield, 1.83 g, 95% purity).

[0035] Aromatization

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

Embodiment 2

[0038] Chlorination

[0039] 10 mmol of 7-bromo-3,4-dihydronaphthalene-1(2H)-one (2.25 g), 20 mmol of triphenoxyphosphorus (6.2 g) were added to 200 mmol of CCl under nitrogen atmosphere 4 (19.3 mL), stirred at room temperature for 30 min, then heated to reflux and continued the reaction for 5 h. After the reaction, it was lowered to room temperature, and CCl was added. 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

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

Embodiment 3

[0043] The chlorination reaction is the same as in Example 1.

[0044] Aromatization

[0045] In a nitrogen atmosphere, 5mmol of 6-bromo-4-chloro-1,2-dihydronaphthalene (1.22g) and 15mmol of TEMPO (2.34g) were added to 100mmol of toluene (10.6mL) and reacted at room temperature for 16h. After the reaction was completed, 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-bromo-1-chloronaphthalene, which uses 7-bromo-3,4-dihydronaphthalene-1(2H)-one as a raw material to make 7-bromo-3,4-dihydronaphthalene Hydronaphthalene-1(2H)-ketone, phosphorus reagent and carbon tetrachloride mix, carry out chlorination reaction, generate 6-bromo-4-chloro-1,2-dihydronaphthalene; make 6-bromo-4-chloro- 1,2-dihydronaphthalene is subjected to an aromatization reaction under the action of an oxidant to generate 7-bromo-1-chloronaphthalene; this reaction route is not only shorter than the synthesis method in the prior art, but also uses safer reagents , easy to handle, easy to carry out large-scale production, good yield.

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 novel norepinephrine, dopamine, and serotonin reuptake inhibitors (US2006052378(A1)), but also an intermediate of various new optoelectronic 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 a raw material, and hydrochloric acid The hydroxylamine reaction generates the corresponding oxime; (2) the oxime is subjected to aromatization reaction in the mixed system of concentrated sulfuric acid and acetic anhydride to generate the corresponding 7-bromo-1-naphthylamine; (3) 7-bromo-1-...

Claims

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Application Information

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Patent Type & Authority Patents(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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