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为研究棉田除草剂溴嘧氯草醚(开发代号SIOC0426,化学名称为N-[2-氯-6-(4,6-二甲氧基-2-嘧啶氧基)苄基]-4-溴苯胺)的中试合成工艺,以2-氟-6-氯苯甲醛为起始原料,通过水解、缩合、还原和亲核取代反应在公斤级规模上合成了溴嘧氯草醚,用高效液相色谱外标法测定了原药含量,通过三维高效液相色谱-质谱联用(HPLC-DAD-MS)技术对原药中的杂质结构进行了鉴定。结果表明,反应总收率高于80%,原药含量大于98%,主要杂质为未反应完全的中间体2-[(4-溴苯氨基)甲基]-3-氯苯酚和溴嘧氯草醚Smiles重排产物。该工艺反应条件温和,反应收率高,原药含量高,“三废”排放较少,较适合工业化放大生产。
In order to study the cotton field herbicide bromoxazol (under the development code SIOC0426, the chemical name is N- [2-chloro-6- (4,6-dimethoxy-2-pyrimidinyloxy) benzyl] Aniline) in the pilot-scale synthesis process, 2-Fluoro-6-chlorobenzaldehyde as starting material, by hydrolysis, condensation, reduction and nucleophilic substitution reaction in the kilogram scale synthesis of bromoxynil ether, with high performance liquid phase The external standard method was used to determine the content of the crude drug. The impurity structure in the crude drug was identified by HPLC-DAD-MS with three-dimensional high performance liquid chromatography-mass spectrometry (HPLC-DAD-MS) The results showed that the total yield of the reaction was higher than 80% and the original content was more than 98%. The main impurities were 2 - [(4 - bromophenylamino) methyl] -3 - chlorophenol and bromoxetane Grass ether Smiles Rearranged product. The process has the advantages of mild reaction conditions, high reaction yield, high original drug content, less emission of “three wastes” and more suitable for industrialized amplification.