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Preparation method of 3, 5-dimethyl-4-bromomethylbenzonitrile

A technology of bromomethyl benzonitrile and dimethyl, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of difficult to obtain target compounds with high selectivity, high requirements for equipment and environment, casualties and other problems, and achieve good industrial Application prospect, lower production cost, lower risk effect

Active Publication Date: 2012-08-22
暨明医药科技(苏州)有限公司
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Problems solved by technology

[0002] Benzonitrile compounds are important basic components for the synthesis of various drugs, and the compound 3,5-dimethyl-4-bromomethylbenzonitrile is an important intermediate for the preparation of various drugs. For this type of multi-substituted benzonitrile Nitrile compound, because of its many functional groups, it is often difficult to prepare the target compound with high selectivity
In the prior art, similar benzonitrile compounds are generally synthesized by heating phenyl bromide and metal cyanide, but metal cyanide has severe toxicity, and a little carelessness may cause casualties and damage equipment. High environmental requirements, great damage to the external environment, complicated follow-up processing, and high production costs

Method used

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  • Preparation method of 3, 5-dimethyl-4-bromomethylbenzonitrile
  • Preparation method of 3, 5-dimethyl-4-bromomethylbenzonitrile

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Embodiment

[0022] In this embodiment, a kind of preparation method of multi-substituted benzonitrile compound, its synthetic route is as follows figure 1 Shown:

[0023] 1. Preparation of 2,6-dimethyl-4-bromoiodobenzene (1)

[0024] Add 200 g of 2,6-dimethyl-4-bromoaniline to 1 liter of hydrochloric acid, cool the mixture to 0-5°C, and slowly add 69 g of sodium nitrite aqueous solution dropwise under vigorous stirring. During the dropwise addition, the temperature of the reaction system was controlled to be lower than 5°C. After the addition was complete, the reaction was carried out for 1 hour. Then it was slowly added dropwise to 332 grams of potassium iodide aqueous solution, and after the addition was completed, it was reacted at 45-60°C for 2 hours. Cool to room temperature 20-35°C, extract the aqueous phase 3 times with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, concentrate and add an appropriate amount of petroleum ether, crystallize to obtain...

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Abstract

The invention discloses a preparation method of 3, 5-dimethyl-4-bromomethylbenzonitrile. The preparation method comprises the following steps: selectively synthesizing an important intermediate, namely aryl aldehyde by utilizing a Grignard reagent and different exchange capacities of bromine and iodine in 2, 6-dimethyl-4-bromoiodobenzene, reducing to get benzyl alcohol, then utilizing halogen-lithium exchange reaction to get an aryl aldehyde compound, further reacting with hydroxylamine to get oxime, dehydrating to get cyan and further synthesizing the 3, 5-dimethyl-4-bromomethylbenzonitrile. According to the preparation method disclosed by the invention, a highly toxic metal cyanide can be avoided, the risk is reduced, and the preparation method is more environment-friendly and in line with the aim of green chemistry; and simultaneously, the route is simple and convenient to operate, the complex post-treatment process is avoided, the production cost is reduced, and the preparation method further has great industrial application prospects.

Description

technical field [0001] The invention relates to the field of preparation of pharmaceutical intermediates, in particular to a preparation method of a multi-substituted benzonitrile compound 3,5-dimethyl-4-bromomethylbenzonitrile. Background technique [0002] Benzonitrile compounds are important basic components for the synthesis of various drugs, and the compound 3,5-dimethyl-4-bromomethylbenzonitrile is an important intermediate for the preparation of various drugs. For this type of multi-substituted benzonitrile Nitrile compounds, because of their many functional groups, are often difficult to prepare target compounds with high selectivity. In the prior art, similar benzonitrile compounds are generally synthesized by heating phenyl bromide and metal cyanide, but metal cyanide has severe toxicity, and a little carelessness may cause casualties and damage equipment. The environmental requirements are high, the damage to the external environment is great, the follow-up proce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/00
Inventor 李斌峰陈建戈苑可孙涛
Owner 暨明医药科技(苏州)有限公司
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