Synthesis method for 5-bromo-ethyl levulinate

A technology of ethyl bromolevulinate and ethyl acetoacetate, which is applied in the field of synthesis of the pharmaceutical intermediate 5-ethyl bromolevulinate, can solve the problems of difficult industrial production, high economic cost, and many by-products, and achieve The effect of high conversion rate, simple synthesis method and mild reaction conditions

Inactive Publication Date: 2013-04-10
XIAMEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have high economic cost, low yield and many by-products, so it is not easy to widely promote industrialized production

Method used

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  • Synthesis method for 5-bromo-ethyl levulinate
  • Synthesis method for 5-bromo-ethyl levulinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of ethyl 5-aminolevulinate intermediate product, ethyl 5-bromolevulinate.

[0022] Mix ethyl levulinate (14.4g) with 100ml of absolute ethanol, add 16g of liquid bromine dropwise to the medium for 2 hours, react at 35°C for 4 hours under stirring conditions, and obtain a light yellow transparent liquid. Take 1ml of the reaction solution, and detect the content of ethyl 5-bromolevulinate by gas chromatography. The selectivity of ethyl 5-bromolevulinate can reach 60%.

[0023] After taking 200g of the reaction solution and distilling ethanol under reduced pressure at 45°C, add 200ml of anhydrous ether and 10ml of water respectively, let stand to separate the water phase, and use a large amount of saturated Na 2 CO 3 solution to wash the organic phase, then anhydrous MgSO 4 After drying and distilling off the ether, the brominated mixture was obtained, dissolved in a mixed solvent of ether and cyclohexane (volume ratio: 1:1), cooled to crystallize, and then ...

Embodiment 2

[0025] Preparation of ethyl 5-aminolevulinate intermediate product, ethyl 5-bromolevulinate.

[0026] Mix ethyl levulinate (14.4g) with 50ml of absolute ethanol, add 16g of liquid bromine dropwise to the medium for 2 hours, and react at 35°C for 8 hours under stirring conditions to obtain a light yellow transparent liquid. Take 1ml of the reaction solution, and detect the content of ethyl 5-bromolevulinate by gas chromatography. The selectivity of ethyl 5-bromolevulinate reached 47.4%.

[0027] Take 300g of the reaction solution and distill ethanol under reduced pressure at 45°C, add 300ml of anhydrous ether and 30ml of water respectively, let stand to separate the water phase, and use a large amount of saturated Na 2 CO 3 solution to wash the organic phase, then anhydrous MgSO 4 After drying and distilling off the ether, the brominated mixture was obtained, dissolved in a mixed solvent of ether and cyclohexane (volume ratio: 1:1), cooled to crystallize, and then recrystall...

Embodiment 3

[0029] Preparation of ethyl 5-aminolevulinate intermediate product, ethyl 5-bromolevulinate.

[0030] Mix ethyl levulinate (14.4g) with 50ml of absolute ethanol, add 16g of liquid bromine dropwise to the medium for 2 hours, and react at 5°C for 2 hours under stirring conditions to obtain a light yellow transparent liquid. Take 1ml of the reaction solution, and detect the content of ethyl 5-bromolevulinate by gas chromatography. The selectivity of ethyl 5-bromolevulinate reached 30.1%.

[0031] After taking 200g of the reaction solution and distilling ethanol under reduced pressure at 45°C, add 200ml of anhydrous ether and 10ml of water respectively, let stand to separate the water phase, and use a large amount of saturated Na 2 CO 3 solution to wash the organic phase, then anhydrous MgSO 4 After drying and distilling off the ether, the brominated mixture was obtained, dissolved in a mixed solvent of ether and cyclohexane (volume ratio: 1:1), cooled to crystallize, and then ...

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Abstract

A synthesis method for 5-bromo-ethyl levulinate relates to a 5-aminolevulinic acid. Ethyl levulinate and liquid bromine are used as raw materials. The provided synthesis method for the 5-bromo-ethyl levulinate has the advantages of simplicity, wide raw material source, cheap raw materials, high yield and easiness in industrial production. The synthesis method comprises the following steps of: adding the ethyl levulinate raw material and a solvent into a reactor and reacting, and in the reaction process, adding the liquid bromine into the reactor to carry out bromination reaction; after the reaction is over, recycling the solvent in reaction liquid by a reduced pressure distillation method; dissolving distillation residues by water, adding diethyl ether for extraction, and obtaining a diethyl ether layer; washing the diethyl ether layer by a saturated sodium carbonate solution until the pH (Potential of Hydrogen) of the diethyl ether layer is neutral; drying and filtering by anhydrous magnesium sulfate, and recycling the diethyl ether through distillation so as to obtain a 5-bromo-ethyl levulinate crude product; and dissolving the 5-bromo-ethyl levulinate crude product in a mixed solvent of the diethyl ether and cyclohexane, and carrying out cooling crystallization in a cold trap to obtain the 5-bromo-ethyl levulinate.

Description

technical field [0001] The invention relates to a kind of 5-aminolevulinic acid, in particular to a method for synthesizing a medicine intermediate ethyl 5-bromolevulinate. Background technique [0002] As a new generation of photodynamic drugs, 5-aminolevulinic acid and its lipid derivatives have great application value in the diagnosis and treatment of brain tumors, skin cancer and other diseases. Ethyl 5-bromolevulinate is an important intermediate in the synthesis of ethyl 5-aminolevulinate from ethyl levulinate to obtain high yield and high purity ethyl 5-bromolevulinate to 5 -Acquisition of ethyl aminolevulinate is very important. At present, there are very few reports about the synthesis of this intermediate at home and abroad. [0003] The production method of 5-aminolevulinic acid can be divided into microbial fermentation method and chemical synthesis method. Microbial fermentation has the advantages of cheap and easy-to-obtain raw materials and good environment...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/716C07C67/307
Inventor 孙勇林鹿郝唯唯
Owner XIAMEN UNIV
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