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Preparation method of 5-bromolevulinic acid

A kind of technology of bromolevulinic acid and trifluoroacetic acid, applied in the field of preparation of 5-bromolevulinic acid, can solve the problem of not finding the preparation of 5-bromolevulinic acid, etc., and achieve the effect of high raw material utilization rate

Inactive Publication Date: 2019-03-01
HUBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In summary, although alkyl halide alkynes can be converted into α-halomethyl ketones according to the above method, there is currently no search for the use of 5-bromo-4-pentynoic acid as a raw material for the preparation of 5-bromolevulinic acid Methods

Method used

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  • Preparation method of 5-bromolevulinic acid
  • Preparation method of 5-bromolevulinic acid
  • Preparation method of 5-bromolevulinic acid

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preparation example Construction

[0026] A preparation method of 5-bromolevulinic acid, comprising the steps of: dissolving 5-bromo-4-pentynoic acid in a solvent, then adding water, copper (II) salt and ligand at 25-90°C After reacting for 4-6 hours, 5-bromolevulinic acid is isolated; wherein, the ligand is at least one selected from 1,10-phenanthroline or its derivatives.

[0027] The preparation method of 5-bromolevulinic acid provided by the embodiments of the present invention is to dissolve 5-bromo-4-pentynoic acid in a solvent as a raw material, and after adding water, add copper (II) salt and 1,10-phenanthrene Roline or derivatives thereof are heated and reacted as a ligand, thereby preparing 5-bromolevulinic acid, and its specific reaction equation is as follows:

[0028]

[0029] The preparation method of 5-bromolevulinic acid provided by the embodiment of the present invention can obtain 5-bromolevulinic acid with high selectivity, and the yield is high, and the method for preparing 5-bromolevulin...

Embodiment 1

[0039] The embodiment of the present invention provides a kind of 5-bromolevulinic acid, and its specific preparation method comprises the following steps:

[0040] Prepare a 100mL flask, dissolve 0.531g of 5-bromo-4-pentynoic acid (3.0mmol) into 36mL of TFA, stir well and add 0.162mL of water (9.0mmol), 0.048g of anhydrous copper sulfate (0.30mmol ), heated to 70°C for 4h, evaporated the solvent under reduced pressure, and separated by column chromatography (using ethyl acetate / petroleum ether=1:3 eluent to wash the adsorption column) to obtain 0.374g of 5-bromolevulinic acid , the yield was 64%.

Embodiment 2

[0042] Embodiment 2 is similar to the implementation steps of Example 1, but the catalyst anhydrous copper sulfate is changed to 0.040g anhydrous copper chloride (0.30mmol), and other steps are the same as in Example 1 to obtain 5-bromolevulinic acid 0.404g , the yield was 69%.

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Abstract

The invention discloses apreparation method of 5-bromolevulinic acid, and belongs to the field of chemical preparation. The preparation method of the 5-bromolevulinic acid comprises the following steps: dissolving 5-bromo-4-pentinoic acid in a solvent; then adding water, copper salt (II) and a ligand for reacting at a temperature of 25 to 90 DEG C for 4 to 6 hours; performing separation to obtain5-bromolevulinic acid, wherein the ligand is selected from at least one of 1,10-phenanthroline or a derivative thereof. By adopting the preparation method of the 5-bromolevulinic acid provided by theinvention, the side product of 3-bromolevulinic acid is avoided, and high raw material utilization rate, easiness in product separation and high yield are achieved.

Description

technical field [0001] The invention relates to the field of chemical preparation, and in particular to a preparation method of 5-bromolevulinic acid. Background technique [0002] 5-bromolevulinic acid is an important α-halogenated ketone compound, which can be used as a raw material to prepare products such as 5-aminolevulinic acid and ranunculolactone, 4,5-dihydropyridazinone derivatives, Among them, 4,5-dihydropyridazinone derivatives have the effect of dilating blood vessels, small ranunculolide can be used to treat tuberculosis, and 5-aminolevulinic acid can be used for various skin diseases, acne, upper gastrointestinal cancer, breast cancer, etc. Cancer, genital warts, rheumatoid arthritis, port wine stains, age-related macular degeneration and other diseases. In addition, in the agricultural field, 5-aminolevulinic acid can be used as a pesticide and a plant growth regulator. On the one hand, it can promote photosynthesis function, improve the efficiency of photosy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/373C07C59/21
CPCC07C51/373C07C59/21
Inventor 张万轩胡博刘泽
Owner HUBEI UNIV
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