Synthesis of 2-bromine-4-nitrobenzene ethane nitrile

A technology of nitrophenylacetonitrile and p-nitrophenylacetonitrile, applied in the field of synthesis of 2-bromo-4 nitrophenylacetonitrile, achieving the effects of less energy consumption, simple operation and high yield

Inactive Publication Date: 2009-04-08
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the synthetic method of 2-bromo-4-nitrophenylacetonitri

Method used

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  • Synthesis of 2-bromine-4-nitrobenzene ethane nitrile
  • Synthesis of 2-bromine-4-nitrobenzene ethane nitrile

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Experimental program
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Embodiment 1

[0015] Embodiment 1, a kind of synthetic method of 2-bromo-4-nitrophenylacetonitrile, take phenylacetonitrile as main raw material, successively through the following steps:

[0016] 1) Nitration: Add 178.4mL of concentrated nitric acid and 267.2mL of concentrated sulfuric acid to a 1000mL three-neck flask, cool in an ice-water bath to 5°C, add 64mL of phenylacetonitrile dropwise, and control the temperature not to exceed 10°C. After the addition, remove the ice-water bath and warm up slowly Continue the reaction at room temperature (25° C.) for 2 h, then pour the obtained reaction product into 2500 g of ice water with stirring to produce a light yellow solid, which is filtered to obtain a filter cake. The filter cake was washed with water until neutral, and dried to obtain 62.5 g of p-nitrophenylacetonitrile, mp: 114-115°C, yield 69.1%.

[0017] 2) Bromination: Add 50.0 mL of concentrated sulfuric acid to a 250 mL three-necked flask, cool to -20°C with a low-temperature therm...

Embodiment 2

[0020] Embodiment 2, a kind of synthetic method of 2-bromo-4-nitrophenylacetonitrile, take phenylacetonitrile as main raw material, successively through the following steps:

[0021] 1) Nitration: Add 74.4mL of concentrated nitric acid and 372.0mL of concentrated sulfuric acid to a 1000mL three-neck flask, add 64mL of phenylacetonitrile dropwise at room temperature (25°C), control the temperature not to exceed 30°C, and continue the reaction at room temperature (25°C) after the addition After 3 hours, the resulting reaction product was poured into 1000 g of ice water with stirring, and a light yellow solid was produced immediately, which was filtered to obtain a filter cake. The filter cake was washed with water until neutral, and dried to obtain 41.3 g of p-nitrophenylacetonitrile, mp: 114-115°C, yield 45.7%.

[0022] 2) Bromination: In a 250mL three-necked flask, add 88.0mL of concentrated sulfuric acid, cool in an ice-water bath to -20°C, add 16.2g of p-nitrophenylacetonitr...

Embodiment 3

[0024] Embodiment 3, a kind of synthetic method of 2-bromo-4-nitrophenylacetonitrile, take phenylacetonitrile as main raw material, successively through the following steps:

[0025] 1) Nitration: Add 186.1mL of concentrated nitric acid and 186.1mL of concentrated sulfuric acid to a 1000mL three-neck flask, and control the reaction temperature at -20°C in a low-temperature thermostat; add 64mL of phenylacetonitrile dropwise, and control the temperature not to exceed -10°C. After the addition- The reaction was continued at 20°C for 0.5 h; then the obtained reaction product was poured into 5000 g of ice water with stirring, and a pale yellow solid was formed immediately, which was filtered to obtain a filter cake. The filter cake was washed with water until neutral, and dried to obtain 59.6 g of p-nitrophenylacetonitrile, mp: 114-115°C, yield 65.9%.

[0026] 2) Bromination: In a 250mL three-necked flask, add 26.4mL of concentrated sulfuric acid, add 16.2g of p-nitrophenylacetoni...

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Abstract

The invention discloses a synthesis method for 2-bromine-4-nitryl phenylacetonitrile. The synthesis method uses phenylacetonitrile as a main starting material and comprises the following: 1) a step of nitrifying: stirring the phenylacetonitrile in mixed acid consisting of concentrated sulfuric acid and concentrated nitric acid to react, putting the obtained reaction product in ice water, separating out solid for filtering to obtain precipitate, and then washing the precipitate by water and drying the precipitation in turn to obtain n-nitro-phenylacetonitrile; and 2) a step of bromizing: dissolving the n-nitro-phenylacetonitrile in the concentrated sulfuric acid, adding N-bromosuccinimide to bromize, putting the obtained reaction mixture in the ice water, separating out solid for filtering to obtain precipitate, and then washing the precipitate by water and drying the precipitate in turn to obtain the 2-bromine-4-nitryl phenylacetonitrile. The 2-bromine-4-nitryl phenylacetonitrile synthesized by the method has the characteristics of simple technique, low cost and high yield.

Description

technical field [0001] The present invention relates to a kind of synthesis method of organic compound, especially the synthesis method of 2-bromo-4 nitrophenylacetonitrile. Background technique [0002] The molecular formula of 2-bromo-4-nitrophenylacetonitrile is shown in I, and it is the key intermediate of synthetic antibiotic medicine. But the synthetic method of 2-bromo-4-nitrophenylacetonitrile all has no open literature report both at home and abroad. [0003] Contents of the invention [0004] The technical problem to be solved by the present invention is to provide a synthetic method of 2-bromo-4-nitrophenylacetonitrile with simple process, low cost and high yield. [0005] In order to solve the above-mentioned technical problems, the invention provides a kind of synthetic method of 2-bromo-4-nitrophenylacetonitrile: take phenylacetonitrile as main starting raw material, comprise the following steps successively: [0006] 1), Nitration: phenylacetonitrile is...

Claims

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Application Information

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IPC IPC(8): C07C255/35C07C253/30
Inventor 陈新志刘金强
Owner ZHEJIANG UNIV
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