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Preparation method of N-(4-bromobenzene)-N-phenyl-1-naphthylamine

A technology of bromophenyl and phenyl, which is applied in the field of preparation of naphthylamine, can solve the problems of high cost, difficult industrial production, high temperature, etc., and achieve the effect of increasing yield

Active Publication Date: 2015-04-01
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Palladium catalysts are used in the prior art, and palladium is not easy to recycle, the cost is high, the temperature is high, and it is not easy for industrial production

Method used

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  • Preparation method of N-(4-bromobenzene)-N-phenyl-1-naphthylamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Under the protection of nitrogen, add 70ml of dichloromethane and 14g (0.084mol) of N-phenyl-1-naphthylamine into a 250ml four-necked bottle, stir well, and add 8g of sodium tert-butoxide and 1.6g of catalyst cuprous iodide after completely dissolving Then add 23.8g of p-bromoiodobenzene, stir well, increase the temperature to 30°C, TLC traces until the reaction is complete, change the device to recover part of the solvent by distillation under reduced pressure, then add 50ml of water, stir, solids are precipitated, and the crude product is filtered. Wash with water, and finally ethanol recrystallization. 13.7 g of the product was obtained with a molar yield of 75.1%.

Embodiment 2

[0023] Comparative experiment: under the protection of nitrogen, add 70ml of toluene and 14g (0.084mol) of N-phenyl-1-naphthylamine into a 250ml four-necked bottle, stir well, and add 8g of sodium tert-butoxide after completely dissolving, catalyst ditriphenylphosphine Add 0.7g of palladium dichloride, then add 23.8g of p-bromoiodobenzene, stir fully, raise the temperature to 80-90°C, follow up with TLC until the reaction is complete, change the device to recover part of the solvent by distillation under reduced pressure, then add 50ml of water, stir, there is Solids were precipitated, and the crude product was washed with water after filtration, and finally recrystallized from ethanol. 9.1 g of the product was obtained, and the molar yield was 50.1%.

[0024] Through Examples 1 and 2, we can draw that the molar yield of the present invention is significantly improved.

Embodiment 3

[0026] Under the protection of nitrogen, add 70ml of dichloromethane and 14g (0.084mol) of N-phenyl-1-naphthylamine into a 250ml four-necked bottle, stir well, and add 8g of sodium tert-butoxide and 2.0g of catalyst cuprous iodide after completely dissolving Then add 23.8g of p-bromoiodobenzene, stir well, increase the temperature to 40°C, track the reaction by TLC until the reaction is complete, change the device to recover part of the solvent by distillation under reduced pressure, then add 50ml of water, stir, solids are precipitated, and the crude product is filtered. Wash with water, and finally ethanol recrystallization. 13.7 g of the product was obtained with a molar yield of 79.5%.

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Abstract

The invention discloses a preparation method of N-(4-bromobenzene)-N-phenyl-1-naphthylamine. The method comprises the following components in parts by weight and the following steps of: 1) under the protection of nitrogen, adding 70-100ml of solvent and 14-20 parts of N-phenyl-1-naphthylamine into a reagent bottle, stirring completely, adding 8-15 parts of sodium tert-butoxide and cuprous iodide as a catalyst after the solvent and the N-phenyl-1-naphthylamine are completely dissolved, and then adding 23-30 parts of bromoiodobenzene, and obtaining a reaction solution; and 2) stirring the reaction solution completely, raising the temperature to 20-50 DEG C, carrying out thin-layer chromatography (TCL) tracking till the reaction is completed, and changing a device to recover part of the solvent through decompression and distillation; and then adding 50-100ml of water for stirring, and filtrating after solids are separated out; and obtaining a crude product. According to the invention, a better production process is provided, so that a catalyst is screened to reduce impurities, the yield is improved and the production cost is reduced.

Description

technical field [0001] The present invention relates to the preparation method of naphthylamine, more specifically, the present invention relates to a kind of preparation method of N-(4-bromophenyl)-N-phenyl-1-naphthylamine. Background technique [0002] The structure of N-(4-bromophenyl)-N-phenyl-1-naphthylamine (N-(1-Naphthyl)-N-phenyl-4-bromoaniline) is as follows: [0003] [0004] In the prior art, the preparation method of N-(4-bromophenyl)-N-phenyl-1-naphthylamine is as follows: under nitrogen protection, 70ml of toluene is added in a 250ml four-necked bottle, and N-phenyl- 14g (0.084mol) of 1-naphthylamine, stir well, add sodium tert-butoxide 8g after completely dissolving, catalyst ditriphenylphosphine palladium dichloride 0.7g, then add 23.8g p-bromoiodobenzene, stir well, raise the temperature At 80-90°C, TLC traced until the reaction was complete, changed the device to recover part of the solvent by distillation under reduced pressure, then added 50ml of wate...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/59C07C209/10
Inventor 潘新刚尹志清崔涛文彭剑平陈克喜郑成吴涛
Owner XUZHOU B&C CHEM CO LTD