The preparation method of 2-methoxy-5-bromoaniline

A technology of methoxyl group and bromoaniline is applied in the field of preparation of pharmaceutical intermediate 2-methoxyl group-5-bromoaniline, can solve problems such as being unsuitable for industrial production and few synthesis methods, and achieves cheap raw materials and reaction conditions. mild effect

Inactive Publication Date: 2011-12-14
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It can be seen that the application of 2-methoxyl-5-bromoaniline is very extensive, but there are fewer reports on relevant synthetic methods at present, and they are not all suitable for industrialized production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] (1) Bromination reaction: Add 14.1 g (0.1 mol) of o-fluoronitrobenzene, CH 3 COOH 50 g, ice-water bath temperature control 0 ~ 10 ℃, NBS 17.8 g (0.1 mol) was added in batches under stirring, and kept warm until the reaction was completed. Pour into 100 mL of ice water, separate the organic layer, and wash the water layer with C 2 h 4 Cl 2 (30 mL×2) for extraction, and the organic layers were combined. Anhydrous Na 2 SO 4 Dry and filter with suction. The solvent was removed by rotary evaporation to obtain 20.9 g of 2-fluoro-5-bromonitrobenzene with a yield of 95%.

[0017] (2) Etherification reaction: Add 0.1 mol (22 g) of 2-fluoro-5-bromonitrobenzene to the reaction vessel, CH 3 OH 50 mL, add CH in portions 3 ONa (sodium methoxide) 0.2 mol (10.8 g), stirred and controlled temperature 40 ℃. After the reaction, the product was poured into 100 mL of water. Stand still and filter. The organic layer was separated from the filtrate, the aqueous layer was extracted ...

Embodiment 2

[0020] (1) Bromination reaction: Add 14.1 g (0.1 mol) of o-fluoronitrobenzene, CH 3 COOH 50 g, ice-water bath temperature control 0 ~ 10 ℃, NBS 18.7 g (0.105 mol) was added in batches under stirring, and kept warm until the reaction was completed. Pour into 100 mL of ice water, separate the organic layer, and wash the water layer with C 2 h 4 Cl 2 (30 mL×2) for extraction, and the organic layers were combined. Anhydrous Na 2 SO 4 Dry and filter with suction. The solvent was removed by rotary evaporation to obtain 21.5 g of 2-fluoro-5-bromonitrobenzene with a yield of 98%.

[0021] (2) Etherification reaction: Add 0.1 mol (22 g) of 2-fluoro-5-bromonitrobenzene to the reaction vessel, CH 3 OH 50 mL, add CH in portions 3 ONa 0.3 mol (16.2 g), stirring and controlling the temperature at 40 °C. After the reaction, the product was poured into 100 mL of water. Stand still and filter. The organic layer was separated from the filtrate, the aqueous layer was extracted with Ph...

Embodiment 3

[0024] (1) Bromination reaction: Add 14.1 g (0.1 mol) of o-fluoronitrobenzene, CH 3COOH 50 g, ice-water bath temperature control 0 ~ 10 ℃, NBS 19.6 g (0.11 mol) was added in batches under stirring, and kept warm until the reaction was completed. Pour into 100 mL of ice water, separate the organic layer, and wash the water layer with C 2 h 4 Cl 2 (30 mL×2) for extraction, and the organic layers were combined. Anhydrous Na 2 SO 4 Dry and filter with suction. The solvent was removed by rotary evaporation to obtain 20.2 g of 2-fluoro-5-bromonitrobenzene with a yield of 92%.

[0025] (2) Etherification reaction: Add 0.1 mol (22 g) of 2-fluoro-5-bromonitrobenzene to the reaction vessel, CH 3 OH 50 mL, add CH in portions 3 ONa 0.4 mol (21.6 g), stirred and controlled temperature 40 ℃. After the reaction, the product was poured into 100 mL of water. Stand still and filter. The organic layer was separated from the filtrate, the aqueous layer was extracted with PhCl (30 mL×2)...

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Abstract

The present invention relates to the field of organic synthesis, in particular to a preparation method of 2-methoxy-5-bromoaniline, which uses o-fluoronitrobenzene as a raw material, and undergoes three-step finishing synthesis of bromination, etherification and reduction reactions to obtain a medicine Intermediate 2-methoxy-5-bromoaniline. 2-Methoxy-5-bromoaniline is an important fine chemical intermediate and has a wide range of uses in the pharmaceutical industry. At present, there are few reports on related synthesis methods, and none of them are suitable for industrial production. The invention relates to a preparation method of 2-methoxy-5-bromoaniline. The method uses o-fluoronitrobenzene as a raw material, and undergoes three steps of bromination, etherification and reduction to obtain the pharmaceutical intermediate 2-methoxy-5-bromoaniline, with a total yield of 67.7%. The method of the invention has cheap raw materials and mild reaction conditions, and opens up a process for synthesizing 2-methoxy-5-bromoaniline.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of a pharmaceutical intermediate 2-methoxy-5-bromoaniline. Background technique [0002] 2-Methoxy-5-bromoaniline is widely used as an important pharmaceutical intermediate, for example, it can be synthesized 1) Comppredin disodium phosphate, which has anti-tumor properties. ( Francisco Lara-Ochoa, Georgina Espinosa-Perez. A new synthesis of combretastatins A-4 and AVE-8062A[J]. Tetrahedron Letters 2007, 48(39): 7007-7010 ); 2) Bifenazate, which is a broad class of herbicides, polymers, and natural products, has been designated as a “reduced risk” pesticide by the US Environmental Protection Agency. ( Yoshiaki Kitamura, Ai Sakurai, Hironao Sajiki, et al. Heterogeneous Pd / C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters[J]. Tetrahedron 2007, 63(43): 10596-10602 ); 3) Substituted pyrrolopyrimidine derivatives, which can be u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/02
Inventor 陈兴权丁明杰董燕敏牛纪胜卿鹏程
Owner CHANGZHOU UNIV
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