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A kind of preparation method of 3,4-bis(4-bromophenyl)-1h-pyrrole-2,5-dione

A technology of bromophenyl and diketone, which is applied in the field of diphenyl-1H-pyrrole-2,5-dione and its preparation, can solve the problems of expensive catalyst palladium salt, harsh reaction conditions, and many reaction steps , to achieve the effect of cheap raw materials, short reaction route and mild reaction conditions

Inactive Publication Date: 2019-03-08
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method also has many reaction steps and complex operation, while the Heck reaction conditions are harsh, and the catalyst palladium salt is expensive
Therefore, the application of this reaction has certain limitations

Method used

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  • A kind of preparation method of 3,4-bis(4-bromophenyl)-1h-pyrrole-2,5-dione
  • A kind of preparation method of 3,4-bis(4-bromophenyl)-1h-pyrrole-2,5-dione
  • A kind of preparation method of 3,4-bis(4-bromophenyl)-1h-pyrrole-2,5-dione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] 34.2g (0.2mol) of 4-bromoaniline, 250mL of water, and 88.0g (0.4mol) of 40% fluoroboric acid aqueous solution were added dropwise to a solution of 27.6g (0.4mol) of sodium nitrite and 100mL of water under stirring at 0°C. After the addition was completed, the mixture was raised to room temperature and continued to stir for 2 h. After the reaction was completed, it was filtered with suction to obtain 45.4 g of 4-bromophenyldiazotetrafluoroborate as a white solid with a yield of 84.0%, which was directly used in the next reaction.

Embodiment 2

[0036] 17.1g (0.1mol) of 4-bromoaniline, 150mL of water, 22.0g (0.1mol) of 40% fluoroboric acid aqueous solution were added dropwise at 5°C with a solution of 8.3g (0.12mol) of sodium nitrite and 50mL of water, dropwise After the addition was completed, the mixture was raised to room temperature and continued to stir for 2 hours. After the reaction was completed, it was filtered with suction to obtain 23.9 g of white 4-bromophenyldiazonium tetrafluoroborate with a yield of 88.5%, which was directly used in the next reaction.

Embodiment 3

[0038] Take maleimide 0.97g (0.01mol), cuprous chloride 0.099g (0.001mol), TMEDA 0.116g (0.001mol) into a 50mL round bottom flask, add DMF 15mL, and stir well. Then 2.7 g (0.01 mol) of 4-bromophenylfluoroborate diazonium salt in Example 1 was added in batches, and reacted for 6 hours. TLC monitoring, the reaction is complete, add 10 mL of water, stir for 5 minutes, extract with ethyl acetate, dry the organic phase over anhydrous sodium sulfate, and recrystallize from 95% ethanol to obtain a yellow solid 3,4-bis(4-bromophenyl)-1H- Pyrrole-2,5-dione 1.13g, yield 28%, mp: 216-218°C.

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Abstract

The invention relates to a preparing method for 3,4-bis(4-bromophenyl)-1H-pyrrole-2,5-diketone. The method includes the steps that maleimide, a catalyst and a ligand are added into a solvent to be stirred and added into 4-bromophenyl diazonium tetrafluoroborate in a batched manner, a reaction is carried out for 6 h to 12 h at the temperature of 0 DEG C to 80 DEG C, and the 3,4-bis(4-bromophenyl)-1H-pyrrole-2,5-diketone is obtained through extraction, drying and recrystallization. According to the method, due to the fact that the ligand participates in the reaction, a diphenyl-1H-pyrrole-2,5-diketone compound can be selectively synthesized, and in addition, the method has the beneficial effects that the product yield is high, raw materials are low in cost and easy to obtain, the reaction operation is simple, reaction conditions are moderate, and a reaction line is short; and industrial production is easy.

Description

technical field [0001] The invention belongs to the field of diphenyl-1H-pyrrole-2,5-dione and its preparation, in particular to a kind of 3,4-bis(4-bromophenyl)-1H-pyrrole-2,5-dione Preparation. Background technique [0002] 3,4-bis(4-bromophenyl)-1H-pyrrole-2,5-dione (1) and its derivatives have the activity of inhibiting angiogenesis, therefore, they can be used as an angiogenesis inhibitor to improve Arthritis, psoriasis and many other diseases. (Peifer, C.; Stoiber, T.; Unger, E.; Totzke, F.; Schachtele, C.; Marme, D.; Brenk, R.; Klebe, G.; Scholmeyer, D.; Dannhardt, G.J. Med. . Chem. 2006, 49, 1271-1281). Not only that, but it is also an important organic synthesis intermediate, which has a wide range of applications in the field of radio and television materials and fluorescent probes, and is one of the current research hotspots in the field of materials. (Yeh, H.C.; Chan, L.H.; Wu, W.C.; Chen, C.T.J. Mater. Chem. 2004, 14, 1293-1298., Lee, R.H.; Syu, J.Y.; Huang,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/444B01J31/22
CPCB01J31/1805B01J2231/4277B01J2531/0238B01J2531/16C07D207/444
Inventor 赵圣印杨振华
Owner DONGHUA UNIV
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