有机中间体3,5-二氯苯甲酰氯的合成
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摘要
介绍了一种全新的有机中间体3,5-二氯苯甲酰氯的合成路线,以对氨基苯甲酸为原料以乙酸为溶剂并在三氯化铁的催化下与氯气接触进行氯化反应,再通过低温重氮化反应脱去四号位的氨基,最后与氯化亚砜反应得到目的产物3,5-二氯苯甲酰氯,经过对反应条件参数的优化,最终反应总收率能达到75%以上。本方法具有反应原料易得,价格合适,三废少且反应条件温和等优点,适用于工业化生产。
This paper introduces a new synthetic route of 3,5-dichlorobenzoyl chloride.The p-aminobenzoic acid is used as a raw material,and the acetic acid is used as a solvent to carry out chlorination under the action of ferric chloride.The amino group at the 4 th position is removed by low temperature diazotization.Finally,it is reacted with thionyl chloride to obtain the target product 3,5-dichlorobenzoyl chloride.After optimizing the reaction parameters,the total yield of the reaction is more than 75%.The advantages of this methods include the easy availability and moderate price of starting material,fewer three wastes,and mild reaction conditions.Therefore,this method is suitable for industrial production.
This paper introduces a new synthetic route of 3,5-dichlorobenzoyl chloride.The p-aminobenzoic acid is used as a raw material,and the acetic acid is used as a solvent to carry out chlorination under the action of ferric chloride.The amino group at the 4 th position is removed by low temperature diazotization.Finally,it is reacted with thionyl chloride to obtain the target product 3,5-dichlorobenzoyl chloride.After optimizing the reaction parameters,the total yield of the reaction is more than 75%.The advantages of this methods include the easy availability and moderate price of starting material,fewer three wastes,and mild reaction conditions.Therefore,this method is suitable for industrial production.
引文
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[7] 裴和瑛,孙克,张敏恒.噁嗪草酮合成方法述评[J].农药,2014,53(5):000386-389.
[8] 刘洁.除草剂戊炔草胺的合成研究[D].天津:河北工业大学,2005.
[9] RICHARD.B.D,HARRY.S.3,5-Dichlorobenzoyl chloride[p].Ger Offen.2,418,344.1974-12-19.
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[11] 牛彬波,刘雁,刘伟,等.3,5-二氯苯甲酰氯的合成研究[J].化学试剂,2015,37(2):000176-178.
[12] STEMPEL G H ,GREENE C ,RONGONE R ,et al.Some disubstituted α-Methylstyrenes and their polymerization characteristics and a comparative study of the refractive indexes of substituted styrenes and α-Methylstyrenesr,1[J].Journal of the American Chemical Society,1951,73(1):455-456.
[13] NEWBY.H.Aromatic carboxylic acid[P].Ger offen 968,484,1958-02-27.
[14] KIRSCH.L S.H.3,5-Dichlorobenzoyl chloride [P].Ger.Offen.2,001,491.1974-03-05.
[15] 王倩,孙海超,刘小祥.3,5-二氯苯甲酰氯合成工艺的研究[J].化学与粘合,2018(2).
[16] 朱红星,吴卫忠,朱国彪.3,5-二氯苯甲酸的合成[J].化工进展,2002,21(10):756-757.
[17] 李英利,陈群,蒋晓帆.3,5-二氯苯甲酸的合成研究[J].煤炭与化工,2013,23(3):45-49.
[2] BOYLE C D,KOWALSKI T J.11β-hydroxysteroid dehydrogenase type 1 inhibitors:a review of recent patents[J].Expert opinion on therapeutic patents,2009,19(6):801-825.
[3] MALI J K,TAKALE B S,TELVEKAR V N.Readily switchable one-pot 5-exo-dig cyclization using a palladium catalyst[J].Rsc Advances,2017,7(4):2231-2235.
[4] MA H,ZHUANG C,XU X,et al.Discovery of benzothiazole derivatives as novel non-sulfamide NEDD8 activating enzyme inhibitors by target-based virtual screening.[J].European Journal of Medicinal Chemistry,2017,133:174-183.
[5] 张高宾.三苯胺类敏化染料的合成与光电性能的研究[D].郑州:郑州大学,2013.
[6] 胡晓浩.三苯胺类染料敏化剂的合成及其性能研究[D].上海:华东理工大学,2014.
[7] 裴和瑛,孙克,张敏恒.噁嗪草酮合成方法述评[J].农药,2014,53(5):000386-389.
[8] 刘洁.除草剂戊炔草胺的合成研究[D].天津:河北工业大学,2005.
[9] RICHARD.B.D,HARRY.S.3,5-Dichlorobenzoyl chloride[p].Ger Offen.2,418,344.1974-12-19.
[10] 吴岳林.医药中间体3,5-二氯苯甲酰氯制备和表征[D].南京:南京理工大学,2004.
[11] 牛彬波,刘雁,刘伟,等.3,5-二氯苯甲酰氯的合成研究[J].化学试剂,2015,37(2):000176-178.
[12] STEMPEL G H ,GREENE C ,RONGONE R ,et al.Some disubstituted α-Methylstyrenes and their polymerization characteristics and a comparative study of the refractive indexes of substituted styrenes and α-Methylstyrenesr,1[J].Journal of the American Chemical Society,1951,73(1):455-456.
[13] NEWBY.H.Aromatic carboxylic acid[P].Ger offen 968,484,1958-02-27.
[14] KIRSCH.L S.H.3,5-Dichlorobenzoyl chloride [P].Ger.Offen.2,001,491.1974-03-05.
[15] 王倩,孙海超,刘小祥.3,5-二氯苯甲酰氯合成工艺的研究[J].化学与粘合,2018(2).
[16] 朱红星,吴卫忠,朱国彪.3,5-二氯苯甲酸的合成[J].化工进展,2002,21(10):756-757.
[17] 李英利,陈群,蒋晓帆.3,5-二氯苯甲酸的合成研究[J].煤炭与化工,2013,23(3):45-49.