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Bromo-butanone synthesis method

A technology of bromobutanone and methyl oxopentanoate, applied in the field of biomedicine, can solve problems such as hindering the development and development of downstream products, and achieve the effects of easy promotion, easy availability of raw materials and low price

Inactive Publication Date: 2013-12-18
TIANJIN QUANHECHENG TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no good scale-up production method for the synthesis of bromobutanone, which seriously hinders the development of its downstream products and its further development in the field of biomedicine

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: laboratory synthesis

[0017] 1. Chlorination reaction

[0018] Dissolve methyl 3-oxopentanoate (10g) in anhydrous dichloromethane (50mL), drop the temperature to 0°C and add thionyl chloride (10.4g) dropwise, after the dropwise addition, warm up to room temperature 25°C, stir After 8 hours, TLC detected that the reaction was complete. The reaction solution was directly concentrated to obtain product 2 (11.4 g), with a yield of 90%.

[0019] 2. Degreasing reaction

[0020] Compound 2 (10 g) was dissolved in hydrochloric acid (20 mL), stirred evenly, heated to 80° C. and stirred for 4 hours, and TLC detected that the reaction was complete. Stop heating and drop to room temperature, add water, extract with dichloromethane, combine organic phases, wash with sodium bicarbonate solution, adjust to alkalinity, separate liquid with separatory funnel, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, Product 3 (5.4 g) was obtained after c...

Embodiment 2

[0023] Embodiment 2: small test

[0024] 1. Chlorination reaction

[0025] Dissolve methyl 3-oxopentanoate (100g) in anhydrous dichloromethane (500mL), drop the temperature to 0°C and add thionyl chloride (104g) dropwise. Hours, TLC detected that the reaction was complete. The reaction solution was directly concentrated to obtain product 2 (114g), with a yield of 90%.

[0026] 2. Degreasing reaction

[0027] Compound 2 (100 g) was dissolved in hydrochloric acid (200 mL), stirred evenly, heated to 80° C. and stirred for 4 hours, and TLC detected that the reaction was complete. Stop heating and drop to room temperature, add water, extract with dichloromethane, combine organic phases, wash with sodium bicarbonate solution, adjust to alkalinity, separate liquid with separatory funnel, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, Product 3 (54 g) was obtained after concentration with a yield of 84%.

[0028] 3. Bromination reaction

[0029] Compound...

Embodiment 3

[0030] Embodiment 3: pilot test

[0031] 1. Chlorination reaction

[0032] Dissolve methyl 3-oxopentanoate (1kg) in anhydrous dichloromethane (5L), drop the temperature to 0°C and add thionyl chloride (1.04kg) dropwise, after the dropwise addition, warm up to room temperature 25°C, stir After 8 hours, TLC detected that the reaction was complete. The reaction solution was directly concentrated to obtain product 2 (1.14kg), with a yield of 90%.

[0033] 2. Degreasing reaction

[0034] Compound 2 (1kg) was dissolved in hydrochloric acid (2L), stirred evenly, heated to 80°C and stirred for 4 hours, and the reaction was complete as detected by TLC. Stop heating and drop to room temperature, add water, extract with dichloromethane, combine organic phases, wash with sodium bicarbonate solution, adjust to alkalinity, separate liquid with separatory funnel, wash with saturated sodium chloride, dry over anhydrous sodium sulfate, Product 3 (540 g) was obtained after concentration wit...

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Abstract

The invention relates to a novel bromo-butanone synthesis method. In the method, 3-methyl propionlyacetae is used as a start raw material; a key intermediate is obtained by chlorination and degreasing reactions, wherein the yield is greater than 70%; the bromo-butanone is obtained by bromination, wherein the total yield is greater than 50%. The method provided by the invention can overcome the adverse factors in the enlarged production of bromo-butanone, and has the characteristics of cheap raw materials, short path, no use of dangerous reagent, high yield and the like so that the product can be produced in a large scale and is cheap and convenient to popularize.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a method for synthesizing a drug intermediate. Background technique [0002] Bromobutanone is an important biopharmaceutical intermediate, which can be widely used in the synthesis of various drugs. It has a small molecular weight and a unique structure, and can be derived from a variety of downstream products, so it has a wide range of uses. At present, there is no good scale-up production method for the synthesis of bromobutanone, which seriously hinders the development of its downstream products and its further development in the field of biomedicine. Contents of the invention [0003] The technical problem solved by the present invention is to provide a new method for synthesizing bromobutanone, which can overcome various unfavorable factors in the enlarged production of bromobutanone, and has the advantages of low raw material, short route, no use of dangerous reagents, and hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/16C07C45/63
Inventor 杨廷全王化松王治平刘金文杨芳宋艳民
Owner TIANJIN QUANHECHENG TECH
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