Method for preparing cyanophenyl compound

A compound and benzonitrile technology, applied in the field of chemical intermediate preparation, can solve the problems of high production equipment requirements, large amount of copper nitrate usage, high industrial cost, etc., and achieve the effects of reducing production costs, high product purity, and easy separation and purification

Inactive Publication Date: 2012-09-12
HENAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of copper nitrate in this method is relatively large, and the use of two equivalents of glacial acetic acid and oxygen has high requirements for production equipment. In addition, the use of high-boiling solvent N,N-dimethylformamide brings great problems to product separation. difficulties, these factors will result in higher industrial costs

Method used

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  • Method for preparing cyanophenyl compound
  • Method for preparing cyanophenyl compound
  • Method for preparing cyanophenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 0.5 mmol ethoxybenzene, 0.25 mmol elemental iodine, 0.4 mmol copper nitrate, 0.25 mmol potassium ferricyanide and 2 mL acetonitrile to the reaction tube in sequence. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 180° C., and magnetically stirred at 180° C. for 35 hours. After the reaction was completed, the reaction system was cooled to room temperature. The reacted mixture was purified by column chromatography to obtain 4-ethoxybenzonitrile product with a yield of 73%. use 1 H-NMR and 13 C-NMR confirmed the structure of the product.

Embodiment 2

[0050] Add 0.5mmol benzyloxybenzene, 0.25mmol elemental iodine, 0.4mmol copper nitrate, 0.25mmol potassium ferricyanide and 2.5mL acetonitrile to the reaction tube sequentially. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 180° C., and magnetically stirred at 180° C. for 35 hours. After the reaction was completed, the reaction system was cooled to room temperature. The reacted mixture was purified by column chromatography to obtain 4-benzyloxybenzonitrile product with a yield of 69%. use 1 H-NMR and 13 C-NMR confirmed the structure of the product.

Embodiment 3

[0052]Add 0.5 mmol of 4-fluorobenzylphenyl ether, 0.25 mmol of elemental iodine, 0.4 mmol of copper nitrate, 0.25 mmol of potassium ferricyanide and 1 mL of acetonitrile to the reaction tube in sequence. After the reaction tube was sealed, the reaction tube was placed in an oil bath preheated to 180° C., and magnetically stirred at 180° C. for 35 hours. After the reaction was completed, the reaction system was cooled to room temperature. Purify the reacted mixture by column chromatography to obtain 4-(4-fluorobenzyloxy) benzonitrile product with a yield of 70%. 1 H-NMR and 13 C-NMR confirmed the structure of the product.

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Abstract

The invention relates to a method for preparing a cyanophenyl compound, which comprises the following steps: adding an alkoxy benzene compound, iodine, catalyst copper nitrate, cyanide and an acetonitrile solvent into a reaction vessel in sequence, wherein the weigh ratio of the alkoxy benzene compound to the cyanide, the catalyst copper nitrate and the iodine is 1:(0.1-5):(0.8-1.2):(0.4-0.5), then sealing the reaction container, agitating and reacting for 5-45 hours at a temperature of 150-200 DEG C, cooling to a room temperature after reaction and purifying a reacted mixture through a column chromatography to obtain the cyanophenyl compound. The preparation method has the beneficial effects that the relatively-cheap the alkoxy benzene compound is taken as a raw material, acid and high-pressure gas are not used, the production cost is remarkably reduced, and as low-boiling point solvent acetonitrile is used, a product is easy to separate and purify.

Description

technical field [0001] The invention relates to a method for preparing chemical intermediates, in particular to a method for preparing benzonitrile compounds. Background technique [0002] Benzonitrile compounds are important chemical intermediates. There are many ways to synthesize benzonitrile compounds. There are five main types according to the starting materials: [0003] (1) Using benzamide compounds as raw materials (Indian J. Chem. Sect. B, 2003, 42, 3148-3151), under the action of a dehydrating reagent, one-step dehydration is used to prepare benzonitrile compounds. The reaction formula as follows: [0004] [0005] (2) Using halogenated benzene compounds as raw materials (J. Am. Chem. Soc., 2011, 133, 10999–11005), one-step preparation of benzonitrile compounds by reacting with cyanide, the reaction formula is as follows: [0006] [0007] (3) Use benzaldehyde compounds as raw materials (Synth. Commun., 2004, 34, 2025-2030) to prepare benzonitrile compounds...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C255/54
Inventor 任运来马军营田欣哲王键吉闫孟杰
Owner HENAN UNIV OF SCI & TECH
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