Preparation method of 4-bromoanisole

A technology for bromoanisole and anisole, which is applied in the field of preparation of 4-bromoanisole, can solve the problems of many wastes and high comprehensive cost, and achieves the effects of avoiding pollution, reducing production costs and having high product purity

Inactive Publication Date: 2014-12-24
HENAN UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a kind of preparation method of 4-bromoanisole for solving the above-mentioned technical problem, utilize 1-butyl-3-methylimidazole nitrate as solvent and catalyst, utilize anisole to prepare 4 -Bromoanisole, which overcomes the problems of many wastes and high comprehensive costs in the existing methods

Method used

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  • Preparation method of 4-bromoanisole
  • Preparation method of 4-bromoanisole
  • Preparation method of 4-bromoanisole

Examples

Experimental program
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Embodiment 1

[0025] In the reaction tube, add magneton, 1ml of 1-butyl-3-methylimidazolium nitrate, 0.5mmol of anisole and 0.25mmol of Br 2 (without removing the air from the reaction tube). Then seal the reaction tube at 80 o C under magnetic stirring for 24h. After the reaction was completed, the reaction system was cooled to room temperature, 3 ml of distilled water was added, and the product was extracted with dichloromethane (3×10 mL). The combined organic phases were quantitatively analyzed by gas chromatography, and the gas phase internal standard yield of the product was 86%. The product was separated and purified by column chromatography to obtain 4-bromoanisole product. use 1 H-NMR, 3 C-NMR and 1 The structure of the product was determined by mass spectrometry see Figure 1-3 .

Embodiment 2

[0027] The reaction atmosphere in Example 1 was replaced by oxygen at normal pressure, and other conditions remained unchanged, and the gas phase internal standard yield of the product was 87%.

Embodiment 3-7

[0029] The temperature of reaction in embodiment 1 is changed into 25 respectively o C. 40 o C. 60 o C. 80 o C. 100 o C, with other conditions unchanged, the GC internal standard yields of the products were 54%, 72%, 81%, 86%, and 91%, respectively.

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Abstract

The invention relates to a preparation method of 4-bromoanisole. The preparation method comprises the following steps: under an oxidizing gas atmosphere, dissolving methoxybenzene and liquid bromine into 1-butyl-3-methylimidazole nitrate, and reacting for more than 1h under closed conditions at 25-100 DEG C to obtain a 4-bromoanisole product. The preparation method disclosed by the invention has the advantages that (1) almost all of bromination reagents and raw materials adopted in the preparation method are transformed into the product, and wastes such as hydrobromic acid and the like can be hardly produced; (2) the preparation method is simple in reaction operation, and adopted solvents are hard to volatilize, so that the volatile pollution of organic solvents can be reduced; and (3) the 4-bromoanisole product prepared by using the preparation method is good in purity and high in raw material conversion rate, so that the product quality can be effectively improved, and the production cost can be reduced.

Description

technical field [0001] The invention relates to the technical field of preparation of chemical raw materials, in particular to a preparation method of 4-bromoanisole. Background technique [0002] 4-Bromoanisole is a synthetic raw material for a variety of organic chemicals, such as isooctyl p-methoxycinnamate ultraviolet absorbers that can be used to synthesize avoiding skin damage and preventing skin cancer (Chemical and Biological Engineering, 2012, 29, 47), which can be used to prepare pharmaceutical synthesis intermediates such as 4-methoxyphenethylamine (Chinese patent, patent number: 201210498870.7). The bromination reaction of anisole is one of the effective methods for the synthesis of 4-bromoanisole (Guangzhou Chemical Industry, 2006, 33, 12). Based on this bromination reaction, the main technologies developed at home and abroad are as follows: (1) The method using bromide equivalents as bromination reagents (Adv. Synth. Catal. 2013, 355, 337). This method is gen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/22C07C43/225
CPCC07C41/22
Inventor 王键吉王斌玉任运来梁菊田欣哲王胚
Owner HENAN UNIV OF SCI & TECH
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