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Synthetic method of meta-hydroxyl/methoxyl polybrominated diphenyl ethers

A technology of brominated diphenyl ethers and meta-hydroxyls, which is applied in the field of synthesis of meta-hydroxyl/methoxy polybrominated diphenyl ethers, and can solve problems such as low yield, single product type, and harsh reaction conditions

Inactive Publication Date: 2009-05-06
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can produce mete-OH-PBDEs with 5 bromines, the reaction conditions in the Baeye-Villliger oxidation step are relatively harsh, the yield is very low, and there are many side reactions, and the bromine can only be in the ortho and para positions of the hydroxyl group. Up-substitution, single type of product

Method used

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  • Synthetic method of meta-hydroxyl/methoxyl polybrominated diphenyl ethers
  • Synthetic method of meta-hydroxyl/methoxyl polybrominated diphenyl ethers
  • Synthetic method of meta-hydroxyl/methoxyl polybrominated diphenyl ethers

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Embodiment 1

[0034] Embodiment 1: take 2,4-dibromophenol and 5-fluoro-2-nitroanisole as raw materials to synthesize meta-hydroxyl / methoxy polybrominated diphenyl ethers:

[0035] 1. coupling reaction: 2,4-dibromophenol (2.52g, 10mmol) and 5-fluoro-2-nitroanisole (2.05g, 12mmol), solvent: DMAC (10ml), add anhydrous sodium carbonate ( 10mmol), stirred and refluxed (150°C) for 1.5-2 hours. After the reaction was complete the mixture was extracted. The solvent was removed by rotary evaporation, and the crude product was separated by column chromatography to obtain pure sample A 1 , the structural formula is: Yield 95%, melting point: 139°C.

[0036] 2.A 1 (3.62g, 9mmol) reduction: the reducing agent is iron powder (9mmol), A 1 It was added to a solvent of ethanol (10ml) and acetic acid (10ml) and reacted at 80°C for about 1h. Pure sample A was obtained after extraction and column passing 2 , the structural formula is: Yield 90%, melting point: 88°C. A 2 There are two routes:

[00...

Embodiment 2

[0043] Embodiment 2: 3-aminophenol (6mmol) and 5-fluoro-2-nitroanisole reaction synthesis meta-hydroxyl / methoxy polybrominated diphenyl ethers:

[0044] 1. Coupling reaction: 3-aminophenol (6mmol) and 5-fluoro-2-nitroanisole (5mmol), solvent: DMAC (10ml), add anhydrous sodium carbonate (5mmol), stir and reflux reaction 1.5- 2 hours. After the reaction was complete the mixture was extracted. The solvent was removed by rotary evaporation, and the crude product was separated by column chromatography to obtain pure sample B 1 , the structural formula is: Yield 95%, melting point: 85°C.

[0045] 2.B 1 (1.2g, 4.5mmol) bromine substitution: with glacial acetic acid (10mmol) as solvent, Br 2 (13.5mmol) was added dropwise to B dissolved in glacial acetic acid 1 , the reaction is about 2h, the hydrogen on the ortho and para positions of the amino group is replaced by bromine, and the product is B 2 , the structural formula is: Yield 90%, melting point: 87°C.

[0046] 3. Put B...

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Abstract

The invention relates to a method for synthesizing meta-OH / MeO-PBDEs, which comprises the following steps: the meta-OH / MeO-PBDEs are obtained by taking 2, 4-dibromophenol or aminophenol and 5-fluoro-2-nitroanisole as a raw material through a series of reactions such as a coupling reaction, nitro group reduction, deamination, demethoxylation, bromo-substitution or through a series of reactions such as the coupling reaction, the bromo-substitution, a Sandmeyer reaction, the nitro group reduction, the deamination, the demethoxylation, the bromo-substitution. The method has reasonable reaction conditions and high product purity, and the product purity is usually more than 80 percent. The method has larger practical value to the synthesis of meta-OH / MeO-PBDEs containing more than five bromines (containing five bromines), and provides more standard sample support to the detection of high-bromine PBDE derivatives in the environment. The meta-OH / MeO-PBDEs are generated.

Description

Technical field: [0001] The invention relates to a synthesis method of meta-hydroxyl / methoxy polybrominated diphenyl ether meta-OH / MeO-PBDEs. Background technique: [0002] At present, the synthesis of meta-OH / MeO-PBDEs in the world is mainly carried out by Germany. The team led by Marsh is in progress, but it is mainly aimed at the synthesis of p-or ortho-hydroxyl / methoxy polybrominated diphenyl ethers, and there are many reports of this kind of literature. There are few reports on the synthesis of m-hydroxyl / methoxy PBDEs. The method is mainly prepared by Ullmann coupling reaction between iodide iodide salt and meta-methoxyphenol containing two bromines. Although this method has simple steps and is easy to operate, the number of bromine substitutions on the benzene ring of the final product is very small, and the number of bromines on meta-OH / MeO-PBDEs is only 5 at most, which cannot reach the current detection of more than 5 bromines. Meta-OH / MeO-PBDEs standard sampl...

Claims

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Application Information

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IPC IPC(8): C07C43/295C07C41/22
Inventor 郑柯文高丽萍曹洁郑裕义
Owner SHANGHAI UNIV
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