O-nitrophenol and its derivative synthesis method

A technology of o-nitrophenol and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of strong acid environment pollution, long synthesis steps, and complexity, and achieves the effects of good selectivity and good substrate adaptability.

Active Publication Date: 2015-11-25
HUAWEI TEHCHNOLOGIES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the serious environmental pollution problem caused by the use of strong acid in the synthesis process of o-nitrophenol in the prior art and the problem that the synthesis steps are relatively long and complicated, the present invention proposes a synthesis method of o-nitrophenols and derivatives thereof , the method is simple and efficient

Method used

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  • O-nitrophenol and its derivative synthesis method
  • O-nitrophenol and its derivative synthesis method
  • O-nitrophenol and its derivative synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Take phenol as raw material.

[0036] (2) Add 1.2mmol of phenol, 2mmol of tripotassium phosphate, 0.1mmol of 2-pyridinecarboxylic acid, 1mmol of 2-bromopyridine, 0.05mmol of cuprous iodide, and 2ml of DMSO into a 25ml three-necked flask. Under the protection of argon, the mixture was refluxed at 90°C for 24 hours, and then the reaction was detected by TLC. The resulting mixed solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a light yellow solid 2-(phenoxy yl) pyridine (95% yield).

[0037] (3) Add 0.5 mmol of 2-(phenoxy)pyridine, 0.05 mmol of palladium diacetate, 1.0 mmol of tert-butyl nitrite and 5 ml of 1,2-dichloroethane into a 25 ml sealed pressure vessel in sequence. The mixture was heated and reacted in an 80°C oil bath for 24 hours. After the end of the TLC detection reaction, the reaction solution was diluted with dichloromethane and filtered to obtain a clear liqui...

Embodiment 2

[0042] (1) Take phenol as raw material.

[0043] (2) Add 1.2mmol of phenol, 1.8mmol of tripotassium phosphate, 0.1mmol of 2-pyridinecarboxylic acid, 0.6mmol of 2-bromopyridine, 0.05mmol of cuprous iodide, and 4ml of DMSO into a 50ml three-necked flask. The mixture was refluxed at 90°C for 24 hours under the protection of nitrogen, and TLC detected that the reaction was complete. The resulting mixed solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a light yellow solid 2-(phenoxy) Pyridine (95% yield).

[0044](3) Add 0.5mmol of 2-(phenoxy)pyridine, 0.05mmol of palladium diacetate, 0.5mmol of tert-butyl nitrite and 5ml of 1,2-dichloroethane into a 25ml sealed pressure vessel in sequence. The mixture was heated and reacted in an 80°C oil bath for 24 hours. After the end of the TLC detection reaction, the reaction solution was diluted with dichloromethane and filtered to obtain a clear li...

Embodiment 3

[0049] (1) Take phenol as raw material.

[0050] (2) Add 1.2mmol of phenol, 3mmol of tripotassium phosphate, 0.3mmol of 2-pyridinecarboxylic acid, 0.6mmol of 2-bromopyridine, 0.012mmol of cuprous iodide, and 5ml of DMSO into a 50ml three-necked flask. The mixture was refluxed at 90°C for 30 hours under the protection of argon, and TLC detected that the reaction was complete. The resulting mixed solution was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain a light yellow solid 2-phenoxypyridine (95% yield).

[0051] (3) Add 0.5 mmol of 2-phenoxypyridine, 0.08 mmol of palladium trifluoroacetate, 1.5 mmol of tert-butyl nitrite and 5 ml of 1,2-dichloroethane into a 25 ml sealed pressure vessel in sequence. The mixture was heated and reacted in an 80°C oil bath for 24 hours. After the end of the TLC detection reaction, the reaction solution was diluted with dichloromethane and filtered to obtain a clea...

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Abstract

The invention relates to an organic compound synthesis method. The organic compound synthesis method solves the problem that the existing o-nitrophenol synthesis method utilizes strong acid, produces environmental pollution and has long and complex steps. The invention provides an o-nitrophenol and its derivative synthesis method. The synthesis method comprises that a phenol compound is synthesized into 2-(phenoxy)pyridine, the product 2-(phenoxy)pyridine, a catalyst, tert-butyl nitrite and an organic solvent are orderly added into a sealed pressure-resistant container, the mixed materials are heated in an oil bath at a temperature of 50-100 DEG C and undergo a reaction for 10-30h to produce 2-(2-nitrophenyl)oxypyridine, and the 2-(2-nitrophenyl)oxypyridine is treated to form o-nitrophenol and its derivative. The synthesis method has simple processes and high efficiency.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing an o-nitrophenol compound. Background technique [0002] O-nitrophenol can be used as an intermediate in medicine, dyes, rubber additives and photosensitive materials, and can also be used as a monochromatic pH value indicator, so the preparation of o-nitrophenol is very important. At present, the production process of o-nitrophenol is relatively mature. The traditional method is to use nitric acid as a nitrating agent to nitrate phenol. However, due to the restriction of the substituent effect, the selectivity of o-nitrophenol is poor, and the products are o-nitrophenol and The mixture of p-nitrophenols is difficult to separate. At the same time, due to the oxidizing properties of concentrated nitric acid, the method oxidizes phenol into quinone compounds, resulting in a low yield of o-nitrophenols. For example, Chinese patent CN201210463229.X...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/22C07C205/26
Inventor 刘运奎张巍张剑
Owner HUAWEI TEHCHNOLOGIES CO LTD
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