A green synthetic method for tert-butyl bromoacetate

A technology for green synthesis of tert-butyl bromoacetate, applied in the field of synthesis and preparation of pharmaceutical intermediates, can solve the problems of difficult product separation, low product content, many side reactions, etc., and achieves simple post-processing operation, high reaction yield, Good quality product

Inactive Publication Date: 2017-02-08
周亚丽
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The bromoacetyl chloride used in this route is more toxic, and there are many side reactions in the reaction, which is difficult to separate from the product, and the content of the product obtained is low, and the yield is low
Reaction equipment and production process require harsh conditions, thionyl chloride severely c

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] A kind of green synthesis method of tert-butyl bromoacetate

[0018] Specific steps are as follows:

[0019] Add 139kg (1.0mol) of bromoacetic acid, 400L of tetrahydrofuran, and 17.5kg of perfluorosulfonic acid resin into the reaction kettle, start stirring, raise the temperature to 0°C to 5°C, slowly introduce 67.3kg (1.2mol) of isobutylene gas, and keep warm for 5 Hours, sampling TLC (developing solvent is ethyl acetate: petroleum ether = 3:1) detection, until the bromoacetic acid reaction is complete. Filtrate, recover the perfluorosulfonic acid resin catalyst, rectify after the filtrate is distilled at atmospheric pressure to reclaim the solvent, collect the normal boiling that the top temperature is 160 ℃~165 ℃, obtain 189.2kg tert-butyl bromoacetate, the product purity is 99.5%, and the yield is 97.0% (calculated as bromoacetic acid).

Embodiment 2

[0021] A kind of green synthesis method of tert-butyl bromoacetate

[0022] Specific steps are as follows:

[0023] Add 139kg (1.0mol) of bromoacetic acid, 400L of tetrahydrofuran, and 17.5kg of perfluorosulfonic acid resin into the reaction kettle, start stirring, raise the temperature to 10°C to 15°C, slowly introduce 78.5kg (1.4mol) of isobutylene gas, and keep warm for 5 Hours, sampling TLC (developing solvent is ethyl acetate: petroleum ether = 3:1) detection, until the bromoacetic acid reaction is complete. Filtration, recovery of perfluorosulfonic acid resin catalyst, rectification after filtrate decompression distillation recovery solvent, collection top temperature is 160 ℃ ~ 165 ℃ normal boiling, obtain 190.3kg bromoacetate tert-butyl, product purity 99.6%, yield is 97.6% (calculated as bromoacetic acid).

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PUM

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Abstract

The invention relates to a green synthetic method for tert-butyl bromoacetate. The method is characterized in that bromoacetic acid and isobutylene are adopted as raw materials in the method, a solid superacid is adopted as a catalyst, and the method includes performing an acid-ester esterification reaction at room temperature under atmospheric pressure in an organic solvent, performing filtration after the reaction is finished to recover the catalyst, distilling filtrate to recover the solvent and distilling to obtain the tert-butyl bromoacetate the content of which is 99.0% or above. The reaction yield is 95% or above. The method is high in yield, good in product quality, low in cost, simple in reaction process operation, basically free of generation of three wastes, low in environment pollution, high in operation safety and suitable for industrial production. The catalyst is easily available and can be used repeatedly.

Description

technical field [0001] The invention belongs to the field of synthesis and preparation of pharmaceutical intermediates, in particular to a green synthesis method of tert-butyl bromoacetate. Background technique [0002] Tert-butyl bromoacetate is a light yellow transparent liquid, soluble in alcohol, ether and other organic solvents, used for the synthesis of amino acids and peptide compounds, and is used for the synthesis of cyclic polyamine polycarboxylate contrast agents, cephalosporins, It is an important intermediate of drugs such as receptor antagonists and a common alkylating agent. [0003] There are few domestic production enterprises of tert-butyl bromoacetate, especially there are almost no enterprises with large output, which makes the country have to rely on imports to meet demand, which largely restricts the development of tert-butyl bromoacetate in my country. [0004] There are few reports on the synthesis of tert-butyl bromoacetate in China. "The Simple Syn...

Claims

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Application Information

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IPC IPC(8): C07C67/04C07C69/63
CPCC07C67/04C07C69/63
Inventor 周亚丽
Owner 周亚丽
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