精细化工中间体2024,Vol.54Issue(1) :41-45.DOI:10.19342/j.cnki.issn.1009-9212.2024.01.009

1-(5-溴吡啶-2-基)环丙烷羧酸甲酯的合成

Synthesis of 1-(5-Bromopyridine-2-yl)Cyclopropane Methyl Formate

刘万兴 曹翠莲 刘秀峥 陈文文 王凯
精细化工中间体2024,Vol.54Issue(1) :41-45.DOI:10.19342/j.cnki.issn.1009-9212.2024.01.009

1-(5-溴吡啶-2-基)环丙烷羧酸甲酯的合成

Synthesis of 1-(5-Bromopyridine-2-yl)Cyclopropane Methyl Formate

刘万兴 1曹翠莲 2刘秀峥 2陈文文 2王凯2
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作者信息

  • 1. 聊城市非公有制企业服务中心,山东聊城 252000;聊城市以芳纶为骨架材料的轮胎用绿色粘合体系研究重点实验室,山东聊城 252000
  • 2. 聊城市以芳纶为骨架材料的轮胎用绿色粘合体系研究重点实验室,山东聊城 252000;聊城金歌合成材料有限公司,山东聊城 252000
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摘要

以2-(5-溴-2-吡啶)乙腈和1,2-二溴乙烷为原料,二甲基亚砜为溶剂,经过烷基化反应获得1-(5-溴吡啶-2-基)环丙烷-1-腈(3),水解反应生成1-(5-溴吡啶-2-基)环丙烷羧酸(2),酯化反应生成1-(5-溴吡啶-2-基)环丙烷羧酸甲酯(1).优化反应条件为:投料比n(1,2-二溴乙烷)∶n(2-(5-溴-2-吡啶)乙腈)=1.02∶1.00,n(氢氧化钾)∶n(3)=3.0∶1.0,溶剂二甲基亚砜用量1.8 L,双氧水滴加时间2.0 h,结晶温度-15℃,pH为8.0.优化条件下目标化合物1收率69.5%,纯度98.6%(HPLC).目标化合物的结构经熔点和1HNMR表征确证.

Abstract

Using 2-(5-bromo-2-pyridine)acetonitrile and 1,2-dibromoethane as raw materials and dimethyl sulfoxide as solvent,1-(5-bromo-2-pyridinyl)cyclopropane-1-carbonitrile(3)was obtained through alkylation,1-(5-bromo-2-pyridinyl)cyclopropanecarboxylic acid(2)was formed through hydrolysis,and 1-(5-bromo-2-pyridinyl)cyclopropanecarboxylic acid(methyl 1-(5-bromo-2-pyridinyl)cyclopropanecarboxylate(methyl 1-(5-bromopyridinyl)cyclopropanecarboxylate)was obtained through esterification.The reaction conditions for the chemistry were as follows:n(1,2-dibromoethane)∶n(2-(5-bromo-2-pyridine)acetonitrile)=1.02∶1.00,n(potassium hydroxide)∶n(3)=3.0∶1.0,solvent dimethylsulfoxide dosage of 1.8 L,peroxide dropping time of 2.0 h,crystallization temperature of-15 ℃,and pH 8.0.The yield of target compound 1 under optimised conditions was 69.5%and purity 98.6%(HPLC).The structure of the target compound was confirmed by melting point and 1H NMR characterisation.

关键词

2-(5-溴-2-吡啶)乙腈/1,2-二溴乙烷/合成/核磁

Key words

2-(5-bromo-2-pyridine)acetonitrile/1,2-dibromoethane/synthesis/1H NMR

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出版年

2024
精细化工中间体
湖南化工研究院

精细化工中间体

CSTPCD
影响因子:0.236
ISSN:1009-9212
参考文献量22
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