WO2023240849A1 - 一种氘代芳香化合物的制备方法 - Google Patents

一种氘代芳香化合物的制备方法 Download PDF

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WO2023240849A1
WO2023240849A1 PCT/CN2022/124275 CN2022124275W WO2023240849A1 WO 2023240849 A1 WO2023240849 A1 WO 2023240849A1 CN 2022124275 W CN2022124275 W CN 2022124275W WO 2023240849 A1 WO2023240849 A1 WO 2023240849A1
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anhydride
deuterated
preparation
aromatic compound
aromatic
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高章华
吴涛
陈佳
江之江
唐建波
陶炜坚
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宁波萃英化学技术有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/001—Acyclic or carbocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

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  • the present invention relates to the technical field of organic synthesis, and in particular to a preparation method of deuterated aromatic compounds.
  • Deuterium-containing organics are becoming increasingly important as knowledge of them increases.
  • deuterated reagents such as CDCl 3 , deuterated DMSO, etc. can be used to avoid the interference of hydrogen atoms in ordinary solvents, so that the proportion of hydrogen elements in organic molecules can be accurately analyzed; due to the relatively large mass of deuterium, carbon Deuterium bonds are more stable than carbon-hydrogen bonds, so research on deuterium generation in drugs and functional materials has gradually developed.
  • Aromatic derivatives are an important organic compound and one of the core building blocks of organic synthesis. They can achieve derivatization of a series of functional groups. Therefore, using deuterated aromatic compounds as substrates can further derive a series of deuterated derivatives. Generation of organic compounds. Aromatic derivatives are widely used in functional materials, medicine and petrochemical industry. For example, there have been recent reports that after hydrogen in organic electroluminescent device compounds is replaced with deuterium, the device life, luminous efficiency and other parameters are significantly improved. Aromatic compounds such as anthracene, naphthalene, carbazole, and dibenzofuran are the main building blocks of this type of material.
  • the object of the present invention is to provide a method for preparing deuterated aromatic compounds, using a basic deuterium-containing compound as a deuterium source, and under the action of a suitable acid anhydride, to complete the preparation of deuterated products of aromatic compounds, which has high operability and deuterated properties. It has the advantages of good effect, high deuterium isotope abundance, high product purity and low pollution.
  • the present invention uses low-priced polyfluoric acid anhydride as a catalyst; preferably heavy water is directly used as a deuterium source to deuterate aromatic compounds. It has simple operation, high deuteration degree and yield, simple separation, and the reagent is environmentally friendly.
  • the aromatic compound is selected from benzene, naphthalene, phenanthrene, anthracene, fluorene, carbazole, pyridine, benzopyran, dibenzopyran, benzothiophene, dibenzothiophene, fluoranthene, benzene, Indene, azulene, acenaphthene, biphenyl, 1-phenylnaphthalene, 2-phenylnaphthalene, 9-phenylanthracene, 9-naphthylanthracene, N-phenylcarbazole, N-naphthylcarbazole, benzene One of pyrene, benzoperylene, benzofluoranthene, pyrene, perylene, xanthene, and fluorenocarbazole.
  • the aromatic compound does not contain a substituent, or contains one or more substituents, and the substituent is selected from the group consisting of fluorine, chlorine, bromine, iodine, alkyl, alkoxy, aryl, amino, and hydroxyl. one or more of them.
  • the polyfluoric anhydride is selected from the group consisting of trifluoromethanesulfonic anhydride, perfluoroethylsulfonic anhydride, perfluoropropylsulfonic anhydride, perfluorobutanesulfonic anhydride, trifluoroacetic anhydride, perfluoropropionic anhydride, and perfluorobutane One or more of the acid anhydrides.
  • the deuterium source reagent is selected from one or two of heavy water, deuterated methanol, deuterated ethanol, deuterated isopropyl alcohol, deuterated benzene, and deuterated acid.
  • the inert atmosphere is a gas environment composed of nitrogen or argon.
  • the solvent is selected from one of linear alkanes with 5-10 carbon atoms, branched alkanes with 5-10 carbon atoms, cycloalkanes with 5-10 carbon atoms, and substituted aromatic hydrocarbons.
  • Linear alkanes, branched alkanes, and cycloalkanes with carbon atoms between 5 and 10 can be selected from n-hexane, cyclohexane, methylcyclohexane, n-octane, n-heptane, decalin, etc.
  • Substituted aromatic hydrocarbons can be trifluorotoluene, p-ditrifluorotoluene, o-ditrifluorotoluene, m-ditrifluorotoluene, fluorobenzene, difluorobenzene, hexafluorobenzene, p-fluorochlorobenzene, o-fluorochlorobenzene, m-fluorobenzene Chlorobenzene, chlorobenzene, p-dichlorobenzene, o-dichlorobenzene, m-dichlorobenzene, p-chlorotrifluorotoluene, o-chlorotrifluorotoluene, m-chlorotrifluorotoluene, etc.
  • the present invention utilizes the above-mentioned solvent to improve the solubility of organic matter and solve its sublimation problem.
  • the deuteration reaction temperature is 100-250°C.
  • the amount of solvent used is 2-1200 mL per 100 g of aromatic compounds.
  • the beneficial effects of the present invention are: it can be completed under conventional conditions, the one-pot reaction does not need to replace the solvent midway, and the reaction has high operability and good deuteration effect; the process method has good universality and can be used for a variety of aromatic compounds Preparation of deuterated products; safe, green and cheap.
  • the raw materials and equipment used can be purchased from the market or are commonly used in the field.
  • the methods in the following examples are all conventional methods in the art unless otherwise specified.
  • the aromatic compound is selected from benzene, naphthalene, phenanthrene, anthracene, fluorene, carbazole, pyridine, benzopyran, dibenzopyran, benzothiophene, dibenzothiophene, fluoranthene, benzene, indene, azulene , dihydroacenaphthylene, biphenyl, 1-phenylnaphthalene, 2-phenylnaphthalene, 9-phenylanthracene, 9-naphthylanthracene, N-phenylcarbazole, N-naphthylcarbazole, benzopyrene, One of benzoperylene, benzofluoranthene, perylene, perylene, xanthene, and fluorenocarbazole.
  • the aromatic compound does not contain a substituent, or contains one or more substituents, and the substituent is selected from one of fluorine, chlorine, bromine, iodine, alkyl, alkoxy, aryl, amino, and hydroxyl. species or several species.
  • the polyfluoric anhydride is selected from the group consisting of trifluoromethanesulfonic anhydride, perfluoroethylsulfonic anhydride, perfluoropropylsulfonic anhydride, perfluorobutanesulfonic anhydride, trifluoroacetic anhydride, perfluoropropionic anhydride and perfluorobutyric anhydride. one or more.
  • the deuterium source reagent is selected from one or two types of heavy water, deuterated methanol, deuterated ethanol, deuterated isopropyl alcohol, deuterated benzene, and deuterated acid.
  • the inert atmosphere is a gas environment composed of nitrogen or argon.
  • the solvent is selected from linear alkanes with 5-10 carbon atoms, branched alkanes with 5-10 carbon atoms, cycloalkanes with 5-10 carbon atoms, and substituted aromatic hydrocarbons.
  • the deuteration reaction temperature is 100-250°C.
  • the amount of solvent used is 2-1200mL per 100g of aromatic compounds.
  • Phenanthrene-d 10 Deuterated phenanthrene (Phenanthrene-d 10 ) (4-d), the compound analysis data are as follows: 1 H NMR (399MHz, DMSO-d 6 ) ⁇ 8.81 (s, 0.02H), 7.97 (s, 0.02H), 7.85 (s,0.02H),7.68(s,0.02H),7.64(s,0.02H).MS(EI)188.2.

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  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

提供一种氘代芳香化合物的制备方法，以芳香族化合物为原料，在惰性气氛保护下，在溶剂中，多氟酸酐与氘源试剂作用下发生氘代反应，反应产物经过分离提纯，获得氘代芳香化合物。所述方法具有可操作性高、氘代效果好、氘同位素丰度高、产品纯度高、污染小的优点。

Description

一种氘代芳香化合物的制备方法 技术领域
本发明涉及有机合成技术领域，特别涉及一种氘代芳香化合物的制备方法。
背景技术
随着对含氘有机物认识的增加，含氘有机物变得越来越重要。在核磁检测中，氘代试剂如CDCl 3，氘代DMSO等可以用于避免普通溶剂的氢原子的干扰，从而可以准确地分析出有机分子的氢元素比例；由于氘的质量相对较大，碳氘键比碳氢键更为稳定，所以在药物以及功能材料等方面的氘代研究逐渐发展起来。
芳香族衍生物是一种重要的有机化合物，是有机合成的核心砌块之一，通过它可以实现一系列官能团衍生化，因此以氘代的芳香族化合物为底物可进一步衍生出一系列氘代有机化合物。芳香族衍生物在功能材料、医药以及石油化工等方面有着广泛应用。比如最近有报告，在有机电致发光元件化合物的氢用氘取代后，其元件寿命，发光效率等参数得到明显提高。而蒽、萘、咔唑、二苯并呋喃等芳香族化合物是此类材料的主要砌块。
目前芳香族衍生物的芳香环上的氘代研究仍处于起步阶段，多数氘代芳香硝基衍生物采用化学手段进行制备，且多以经典的有机反应为基础从全氘代苯出发经多步骤的反应制备，反应较为繁杂；近年来，过渡金属对芳香环上的氢氘交换反应的催化有不少文献报道，其中Pt、Pd、Ir、Ni相对较多，比如10％Pd/C在氘气条件下有不错的氘代效果；而酸催化剂是实际工艺中最为常见且回避了贵金属催化剂，价格低廉，其开发相应的方法具有较好的可操作性和稳定性，催化效率高、氘转化率高、产物易分离等特点。但酸催化剂自身带有的酸性氢降低了氘的同位素丰度(氘代度)，不利于高氘代度产品的制备。
发明内容
本发明的目的在于提供一种氘代芳香化合物的制备方法，以基础含氘化合物为氘源，在合适的酸酐作用下，完成芳香族化合物氘代产物的制备，具有可操作性高、氘代效果好、氘同位素丰度高、产品纯度高、污染小的优点。
本发明解决其技术问题所采用的技术方案是：
一种氘代芳香化合物的制备方法，以芳香族化合物为原料，在惰性气氛保护下，在溶剂中，多氟酸酐与氘源试剂存在下，发生氘代反应，反应产物经过分离提纯，获得氘代芳香化合物。本发明使用了价格低廉的多氟酸酐作为催化剂；优选重水直接作为氘源进行芳香族化合物的氘代，操作简单，氘代度及收率高，分离简单，试剂环保友好。
作为优选，所述芳香族化合物选自苯、萘、菲、蒽、芴、咔唑、吡啶、苯并吡喃、二 苯并吡喃、苯并噻吩、二苯并噻吩、荧蒽、蒄、茚、薁、二氢苊、联苯、1-苯基萘、2-苯基萘、9-苯基蒽、9-萘基蒽、N-苯基咔唑、N-萘基咔唑、苯并芘、苯并苝、苯并荧蒽、苉、苝、氧杂蒽、芴并咔唑中的一种。
作为优选，所述芳香族化合物不含取代基，或含有一个或多个取代基，所述取代基选自氟、氯、溴、碘、烷基、烷氧基、芳基、胺基、羟基中的一种或几种。
作为优选，所述多氟酸酐选自三氟甲磺酸酐、全氟乙基磺酸酐、全氟丙基磺酸酐、全氟丁基磺酸酐、三氟乙酸酐、全氟丙酸酐、全氟丁酸酐中的一种或多种。
作为优选，所述氘源试剂选自重水、氘代甲醇、氘代乙醇、氘代异丙醇、氘代苯、氘代酸中一种或两种。
作为优选，所述惰性气氛为由氮气或氩气所构成的气体环境。
作为优选，所述溶剂选择碳原子数在5-10的直链烷烃、碳原子数在5-10的支链烷烃、碳原子数在5-10的环烷烃、取代芳香烃中的一种。
碳原子数在5-10的直链烷烃、支链烷烃、环烷烃可选择正己烷、环己烷、甲基环己烷、正辛烷、正庚烷、十氢萘等。
取代芳香烃可选择三氟甲苯，对二三氟甲苯，邻二三氟甲苯、间二三氟甲苯、氟苯、二氟苯、六氟苯、对氟氯苯、邻氟氯苯，间氟氯苯、氯苯，对二氯苯、邻二氯苯、间二氯苯、对氯三氟甲苯、邻氯三氟甲苯、间氯三氟甲苯等。
本发明利用上述溶剂，提高有机物的溶解度并解决其升华问题。
作为优选，氘代反应温度为100-250℃。
作为优选，溶剂用量为每100g芳香族化合物加2-1200mL。
作为优选，所述多氟酸酐的用量为芳香族化合物的25～70moL％；芳香族化合物：氘源试剂的摩尔比＝1:1.2-10。
本发明的有益效果是：在常规条件下即可完成，一锅法反应无需中途替换溶剂，且反应可操作性高，氘代效果好；工艺方法普适性好，可用于多种芳香族化合物氘代产物的制备；具有安全、绿色、廉价的特点。
具体实施方式
下面通过具体实施例，对本发明的技术方案作进一步的具体说明。
本发明中，若非特指，所采用的原料和设备等均可从市场购得或是本领域常用的。下述实施例中的方法，如无特别说明，均为本领域的常规方法。
Figure PCTCN2022124275-appb-000001
总实施方案：
一种氘代芳香化合物的制备方法，以芳香族化合物为原料，在惰性气氛保护下，在溶剂中，多氟酸酐与氘源试剂作用下发生氘代反应，反应产物经过分离提纯，获得氘代芳香化合物。
所述芳香族化合物选自苯、萘、菲、蒽、芴、咔唑、吡啶、苯并吡喃、二苯并吡喃、苯并噻吩、二苯并噻吩、荧蒽、蒄、茚、薁、二氢苊、联苯、1-苯基萘、2-苯基萘、9-苯基蒽、9-萘基蒽、N-苯基咔唑、N-萘基咔唑、苯并芘、苯并苝、苯并荧蒽、苉、苝、氧杂蒽、芴并咔唑中的一种。
所述芳香族化合物不含取代基，或含有一个或多个取代基，所述取代基选自氟、氯、溴、碘、烷基、烷氧基、芳基、胺基、羟基中的一种或几种。
所述多氟酸酐选自三氟甲磺酸酐、全氟乙基磺酸酐、全氟丙基磺酸酐、全氟丁基磺酸酐、三氟乙酸酐、全氟丙酸酐、全氟丁酸酐中的一种或多种。
所述氘源试剂选自重水、氘代甲醇、氘代乙醇、氘代异丙醇、氘代苯、氘代酸中一种或两种。
所述惰性气氛为由氮气或氩气所构成的气体环境。
所述溶剂选择碳原子数在5-10的直链烷烃、碳原子数在5-10的支链烷烃、碳原子数在5-10的环烷烃、取代芳香烃中的一种。
氘代反应温度为100-250℃。溶剂用量为每100g芳香族化合物加2-1200mL。所述多氟酸酐的用量为芳香族化合物的25～70moL％；芳香族化合物：氘源试剂的摩尔比＝1:1.2-10。
实施例1氘代蒽的合成
于250mL反应器中加入25g的蒽，25mL环己烷，加入25g三氟甲磺酸酐，100g重水，将反应器于220℃下搅拌反应24小时。反应完成后，经GC-MS检测其氘代度为83％。随后经相同操作重复反应4次后，得氘代蒽24.3g(收率95％)，含量97％，氘代度99％。化合物分析数据如下： 1H NMR(399MHz,Chloroform-d)δ8.45(s,0.02H),8.02(s,0.03H),7.47(s,0.06H).MS(EI)188.18。
实施例2氘代咔唑的合成
于250mL反应器中加入咔唑(30g)，30mL环己烷，加入20g三氟乙酸酐，80g重水，将反应器置于于240℃下搅拌反应24小时。反应完成后，经GC-MS检测其氘代度为79％。重复反应4次后，得氘代咔唑24.3g，收率97％，氘代度99％，含量99％。化合物分析数据如下： 1H NMR(399MHz,DMSO-d6)δ8.11(s,0.02H),7.49(s,1,0.02H),7.38(s,0.02H),7.15(s,0.02H)..MS(EI)177.1。
实施例3氘代萘的合成
于250mL反应器中加入萘(50g)，50mL环己烷，加入32g三氟乙酸酐，130g重水，将反应器置于140℃下搅拌反应15小时。反应完成后，经GC-MS检测其氘代度为66％。重复反应4次后，得氘代咔唑53g，收率95％，氘代度97％，含量95％。化合物分析数据如下： 1H NMR(399MHz,DMSO-d6)δ7.91(s,0.04H),7.51(s,1,0.04H).MS(EI)136.1。
从各取代的芳香衍生物出发，在上述条件下得到芳香衍生物氘代产物，其结果如下表所示：
化合物编号 氘代度(％D) 产率(％)
2-d(按照实施例1的方法) 99 93
3-d(按照实施例1的方法) 99 90
4-d(按照实施例2的方法) 99 91
5-d(按照实施例3的方法) 99 88
6-d(按照实施例3的方法) 99 92
7-d(按照实施例2的方法) 98 89
。
氘代苯(benzene-d 6)(2-d). 1H NMR(399MHz,Chloroform-d)δ7.16(s,0.06H),MS(EI)84.1。
氘代9-溴蒽(9-Bromoanthracene-d 9)(3-d)，化合物分析数据如下： 1H NMR(399MHz,DMSO-d 6)δ8.71(s,0.01H),8.39(s,0.02H),8.15(s,0.02H),7.70(s,0.03H),7.59(s,0.03H).MS(EI)266.1。
氘代菲(Phenanthrene-d 10)(4-d)，化合物分析数据如下： 1H NMR(399MHz,DMSO-d 6)δ8.81(s,0.02H),7.97(s,0.02H),7.85(s,0.02H),7.68(s,0.02H),7.64(s,0.02H).MS(EI)188.2。
氘代2-溴咔唑(2-bromo-9H-carbazole-d 7)(5-d)，化合物分析数据如下： 1H NMR(399MHz,DMSO-d 6)δ11.41(s,1H),8.35(s,0.01H),8.16(s,0.01H),7.50(s,0.01H),7.49(s,0.01H),7.45(s,0.01H),7.41(s,0.01H),7.17(s,0.01H).MS(EI)253.1。
氘代3-溴咔唑(3-Bromo-9H-carbazole-d 7)(6-d)，化合物分析数据如下： 1H NMR(399MHz,DMSO-d 6)δ11.41(s,1H),8.12(s,0.01H),8.06(s,0.01H),7.67(s,0.01H),7.51(s,0.01H),7.42(s,0.01H),7.29(s,0.01H),7.18(s,0.01H).MS(EI)253.1。
氘代9-苯基蒽(9-Phenylanthracene-d 9)(7-d)，化合物分析数据如下： 1H NMR(399MHz,Chloroform-d)δ8.51(s,0.04H),8.06(s,0.03H),7.68(s,0.03H),7.59(s,0.02H),7.54(s,0.01H),7.46(s,0.03H),7.45(s,0.03H),7.35(s,0.03H).MS(EI)271.3。
以上所述的实施例只是本发明的一种较佳的方案，并非对本发明作任何形式上的限制，在不超出权利要求所记载的技术方案的前提下还有其它的变体及改型。

Claims (10)

  1. 一种氘代芳香化合物的制备方法，其特征在于，以芳香族化合物为原料，在惰性气氛保护下，在溶剂中，多氟酸酐与氘源试剂作用下发生氘代反应，反应产物经过分离提纯，获得氘代芳香化合物。
  2. 根据权利要求1所述的制备方法，其特征在于，所述芳香族化合物选自苯、萘、菲、蒽、芴、咔唑、吡啶、苯并吡喃、二苯并吡喃、苯并噻吩、二苯并噻吩、荧蒽、蒄、茚、薁、二氢苊、联苯、1-苯基萘、2-苯基萘、9-苯基蒽、9-萘基蒽、N-苯基咔唑、N-萘基咔唑、苯并芘、苯并苝、苯并荧蒽、苉、苝、氧杂蒽、芴并咔唑中的一种。
  3. 根据权利要求1或2所述的制备方法，其特征在于，所述芳香族化合物不含取代基，或含有一个或多个取代基，所述取代基选自氟、氯、溴、碘、烷基、烷氧基、芳基、胺基、羟基中的一种或几种。
  4. 根据权利要求1所述的制备方法，其特征在于，所述多氟酸酐选自三氟甲磺酸酐、全氟乙基磺酸酐、全氟丙基磺酸酐、全氟丁基磺酸酐、三氟乙酸酐、全氟丙酸酐、全氟丁酸酐中的一种或多种。
  5. 根据权利要求1所述的制备方法，其特征在于，所述氘源试剂选自重水、氘代甲醇、氘代乙醇、氘代异丙醇、氘代苯、氘代酸中一种或两种。
  6. 根据权利要求1所述的制备方法，其特征在于，所述惰性气氛为由氮气或氩气所构成的气体环境。
  7. 根据权利要求1所述的制备方法，其特征在于，所述溶剂选择碳原子数在5-10的直链烷烃、碳原子数在5-10的支链烷烃、碳原子数在5-10的环烷烃、取代芳香烃中的一种。
  8. 根据权利要求1所述的制备方法，其特征在于，氘代反应温度为100-250℃。
  9. 根据权利要求1所述的制备方法，其特征在于，溶剂用量为每100g芳香族化合物加2-1200mL。
  10. 根据权利要求1所述的制备方法，其特征在于，所述多氟酸酐的用量为芳香族化合物的25～70moL％；芳香族化合物：氘源试剂的摩尔比＝1:1.2-10。
PCT/CN2022/124275 2022-06-15 2022-10-10 一种氘代芳香化合物的制备方法 WO2023240849A1 (zh)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113149801A (zh) * 2021-01-27 2021-07-23 南京工业大学 氘代多卤素芳香族化合物及其制备方法、有机中间体
WO2022045838A1 (ko) * 2020-08-27 2022-03-03 주식회사 엘지화학 중수소화 방향족 화합물의 제조 방법 및 중수소화 반응 조성물
WO2022045825A1 (ko) * 2020-08-27 2022-03-03 주식회사 엘지화학 중수소화 방향족 화합물의 제조 방법 및 중수소화 반응 조성물
CN114560748A (zh) * 2022-02-28 2022-05-31 山东汉峰新材料科技有限公司 一种氘代苯的生产工艺

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106565600A (zh) * 2016-10-28 2017-04-19 湖南大学 一种氘代氮杂芳香化合物及其合成方法
CN112794798A (zh) * 2019-11-14 2021-05-14 材料科学有限公司 氘化芳香族化合物的中间产物及利用该中间产物的氘化芳香族化合物的制备方法
CN111606774A (zh) * 2020-07-01 2020-09-01 云南民族大学 一种高效制备苯乙烯类及氘代苯乙烯类化合物的方法
CN112876406A (zh) * 2021-01-15 2021-06-01 安徽秀朗新材料科技有限公司 氘代咔唑类化合物及其制备方法、光电材料及药物
CN113526526A (zh) * 2021-07-12 2021-10-22 苏州大学 氘代氨制备方法及以其作为氘源参与的氘代反应
CN113979822A (zh) * 2021-08-30 2022-01-28 浙江工业大学 一种氘代苯类化合物的制备方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022045838A1 (ko) * 2020-08-27 2022-03-03 주식회사 엘지화학 중수소화 방향족 화합물의 제조 방법 및 중수소화 반응 조성물
WO2022045825A1 (ko) * 2020-08-27 2022-03-03 주식회사 엘지화학 중수소화 방향족 화합물의 제조 방법 및 중수소화 반응 조성물
CN113149801A (zh) * 2021-01-27 2021-07-23 南京工业大学 氘代多卤素芳香族化合物及其制备方法、有机中间体
CN114560748A (zh) * 2022-02-28 2022-05-31 山东汉峰新材料科技有限公司 一种氘代苯的生产工艺

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
FIELD, LESLIE D. ET AL.: "Electrophilic Substitution in Naphthalene:Kinetic vs Thermodynamic Control", JOURNAL OF CHEMICAL EDUCATION, vol. 76, no. 9, 30 September 1999 (1999-09-30), pages 1246 - 1247, XP055903932 *

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