T:Toxic;91-23-6Relevant articles and documents
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Ismailski,Rosorenow
, (1923)
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Eco-Friendly Methodology for the Formation of Aromatic Carbon–Heteroatom Bonds by Using Green Ionic Liquids
Richards, Kenza,Petit, Eddy,Legrand, Yves-Marie,Grison, Claude
supporting information, p. 809 - 814 (2020/11/30)
A new sustainable method is reported for the formation of aromatic carbon–heteroatom bonds under solvent-free and mild conditions (no co-oxidant, no strong acid and no toxic reagents) by using a new type of green ionic liquid. The bromination of methoxy arenes was chosen as a model reaction. The reaction methodology is based on only using natural sodium bromine, which is transformed into an electrophilic brominating reagent within an ionic liquid, easily prepared from the melted salt FeCl3 hexahydrate. Bromination reactions with this in-situ-generated reagent gave good yields and excellent regioselectivity under simple and environmentally friendly conditions. To understand the unusual bromine polarity reversal of sodium bromine without any strong oxidant, the molecular structure of the reaction medium was characterised by Raman and direct infusion electrospray ionisation mass spectroscopy (ESI-MS). An extensive computational investigation using density functional theory methods was performed to describe a mechanism that suggests indirect oxidation of Br? through new iron adducts. The versatility of the methodology was successively applied to nitration and thiocyanation of methoxy arenes using KNO3 and KSCN in melted hexahydrated FeCl3.
Cu-Catalyzed Phenol O-Methylation with Methylboronic Acid
Bartlett, Mairead E.,Chavez, Angela K.,Gaffney, Uma Bhagwat,Gorin, David J.,Lee, Joyce,Sharew, Betemariam,Wu, Miranda,Zhu, Yingchuan
supporting information, p. 5661 - 5664 (2021/11/11)
A Cu-catalyzed oxidative cross-coupling of phenols with methylboronic acid to form aryl methyl ethers has been developed, expanding the scope of Chan-Evans-Lam alkylation. Electron-deficient phenol derivatives with a broad array of functional groups are methylated in high yields. Increased reaction temperature and catalyst loading enables the methylation of substrates incorporating pyridine and dihydroquinolone motifs. Electron-rich phenol derivatives are poor substrates for the methylation; the characterization of C?H homodimerization products formed from these substrates illuminates a competing mechanistic pathway.
High-efficiency green production process of o-aminoanisole
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Paragraph 0031-0041, (2021/08/19)
The invention discloses a high-efficiency green production process of o-aminoanisole, which comprises o-chloronitrobenzene and methanol, and the production process comprises the following steps: a, respectively adding the o-chloronitrobenzene, the methanol and a catalyst A into a methoxylation solvent, controlling the temperature at 20-80 DEG C, and adding an alkali in batches to carry out methoxylation reaction, b, filtering and washing the catalyst A-containing mixed solution obtained in the step a to obtain a high-purity intermediate product o-nitroanisole solution; c, directly carrying out hydrogenation reaction on the o-nitroanisole solution in the step b without separation to obtain an o-aminoanisole solution; and d, filtering the o-aminoanisole solution in the step c, removing the solvent, and carrying out reduced pressure distillation to obtain the o-aminoanisole with the purity of 99.5% or above. According to the process, the catalyst A capable of improving the reaction rate is adopted, so that the reaction conditions become milder, the reaction time is shortened, side reactions are greatly inhibited, the catalyst is easy and convenient to recycle, and the continuous application frequency is not less than 20.
