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2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol and preparation method thereof

A technology of endomethylene and nitro, applied in 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-phenol and its In the field of preparation, it can solve problems such as complex operation, poor stability of intermediates, and unsuitability for large-scale industrial production.

Inactive Publication Date: 2017-04-26
杭州百昂锐地科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the currently reported routes have the disadvantages of low yield, difficult access to raw materials, poor stability of intermediates, complex operation, harsh reaction conditions, and unsuitability for large-scale industrial production.
[0005] The synthetic route reported in WO2011131546 is the shortest synthetic route seen in the literature so far, but the starting material 6,6-dichlorofulvene is unstable and needs to be synthesized by itself, so the steps are still relatively long and the overall yield is relatively low; Secondly, this method is a laboratory process, so it is not suitable for large-scale industrial production.

Method used

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  • 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol and preparation method thereof
  • 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol and preparation method thereof
  • 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Example 1 Synthesis of 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-ol (IV)

[0068] The molar ratio of the feed material is [2,3]-epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene (III):48% hydrobromic acid Aqueous solution = 1:10

[0069] In a 500ml three-necked flask equipped with a mechanical stirrer and a thermometer, add 48% hydrobromic acid aqueous solution (177.2g, 1.05mol), and at 20°C, add dropwise [2,3]-epoxy-5-nitro-1 , 130ml of 2,3,4-tetrahydro-1,4-methano-naphthalene (III) (14.3g, 0.07mol) in dichloromethane solution, after 1.5h, the addition was completed, kept stirring for 5min, and analyzed by TLC Track responses. After the reaction was over, let stand to separate the liquids, wash the organic layer twice with 25ml of saturated sodium bicarbonate solution, then wash once with 40ml of saturated brine, separate the layers, dry and concentrate the organic layer to obtain a khaki solid, and wash the crude product with n-hexane...

Embodiment 2

[0071] Example 2 Synthesis of 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-ol (IV)

[0072] The molar ratio of the feed material is [2,3]-epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene (III):48% hydrobromic acid Aqueous solution = 1:5

[0073] 48% hydrobromic acid aqueous solution charging amount is 59.1g, all the other charging amount and operating process are with embodiment 1. 9.7 g of 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol (IV) was obtained, the yield was 49.2%, and the melting point was 132.1°C- 133.3°C, the physical and chemical data are the same as in Example 1.

Embodiment 3

[0074] Example 3 Synthesis of 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-endomethylene-naphthalene-9-ol (IV)

[0075] The molar ratio of the feed material is [2,3]-epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene (III):48% hydrobromic acid Aqueous solution = 1:20

[0076] 48% hydrobromic acid aqueous solution charging amount is 236.2g, all the other charging amount and operating process are with embodiment 1. 11.8 g of 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-ol (IV) was obtained, the yield was 59.6%, and the melting point was 132.1°C- 133.4°C, the physical and chemical data are the same as in Example 1.

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Abstract

The invention provides a chemical compound which can serve as an intermediate for benzovindiflupyr synthesis. The chemical compound is 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol with the chemical formula as shown in formula (IV) in the specification. The invention further provides a method for preparing the chemical compound, 2-bromine-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene-9-phenol. The method comprises: a chemical compound, [2,3]-epoxy-5-nitro-1,2,3,4-tetrahydro-1,4-methano-naphthalene, as shown in formula (III) reacts in a hydrobromic acid aqueous solution at 20 DEG C, and the chemical compound as shown in formula (IV) is prepared. The invention finds a novel method for producing a key intermediate for benzovindiflupyr and a preparation method thereof, thereby enabling the route for benzovindiflupyr synthesis to be more reasonable.

Description

technical field [0001] The present invention relates to a new compound 2-bromo-5-nitro-1,2,3,4-tetrahydro-1,4-methylene-naphthalene-9-ol, its preparation method and application. Background technique [0002] Benzovindiflupyr (also known as SYN545192, trade name Solatenol) is a succinate dehydrogenase fungicide with a new mode of action. Benzofenfluconazole is broad-spectrum, high-efficiency, and has a longer-lasting bactericidal effect. It can widely control foliar diseases and soil pathogens. It is an important tool for resistance management. It is used in many crops such as wheat, corn, and special crops. Demonstrated outstanding control effect on major diseases. The product has a good control effect on wheat leaf blight, peanut black spot, wheat take-all and wheat base rot, especially on wheat powdery mildew, corn small spot and gray mold, and on Asian soybean Rust has excellent control effect and has no cross-resistance with existing fungicides, so it is a fungicide wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/26C07C201/12C07D231/14C07D209/48C07C205/06C07C213/02C07C215/70C07C209/62C07C211/61C07D303/02C07D301/14
CPCC07C205/26C07C201/12C07C209/62C07C213/02C07D209/48C07D231/14C07D301/14C07D303/02C07C205/06C07C215/70C07C211/61
Inventor 姜正金谭志勇李振华王波华
Owner 杭州百昂锐地科技有限公司
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