72326-72-8Relevant articles and documents
Bromination of phenyl ether and other aromatics with bromoisobutyrate and dimethyl sulfoxide
Li, Jia-Qin,Chen, Xiao-Hui,Wang, Xian-Xun,Cui, Hai-Lei
supporting information, (2021/09/09)
Bromoisobutyrate has been used for the first time as a general brominating source for the direct bromination of a diverse of simple phenyl ethers. Aromatic ethers bearing various substituents could be compatible in this reaction system delivering brominated arenes in moderate to good yields. The reaction system can also be expanded to bromination of phenols and unactivated arene. This process can be regarded as an alternative for the well-established bromination systems for bromoarene synthesis.
Efficient synthesis of 5-bromo-2,3-dimethoxy-6-methyl-1,4-benzoquinone: key intermediate for preparing Coenzyme Q
Qiu, Yong-Fu,Lu, Bin,Yan, Yi-Yu,Luo, Wan-Yue,Wang, Jin,Hu, Xiao
, p. 2745 - 2748 (2019/08/21)
The title compound, a key intermediate for preparing Coenzyme Qn family, was prepared in an excellent yield by a reaction sequence starting from the commercially available 3,4,5-trimethoxytoluene 1 via bromination, methoxylation and oxidation reactions. A
Efficient synthesis and antioxidant activities of N-heterocyclyl substituted Coenzyme Q analogues
Wang, Jin,Xia, Fei,Jin, Wen-Bin,Guan, Jin-Yan,Zhao, Hang
, p. 214 - 218 (2016/08/25)
A new strategy for the efficient synthesis of C-5 heterocyclyl substituted Coenzyme Q analogues was developed by N-alkylation of bromomethylated quinone 11 with a series of amines 12 under metal-free conditions. In vitro antioxidant activities of these Coenzyme Q analogues were evaluated and compared with commercial antioxidant Coenzyme Q10 by employing DPPH assay. All these N-heterocyclyl substituted Coenzyme Q analogues are found to be exhibiting good antioxidant properties and may be used as potent antioxidants for combating oxidative stress.
Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning
supporting information, p. 2886 - 2889 (2015/06/30)
An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
Aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide mediated by anthraquinone-2-carboxylic acid
Tanaka, Masanori,Kamito, Yuji,Lei, Cui,Tada, Norihiro,Itoh, Akichika
, p. 5886 - 5888 (2015/11/02)
We developed the aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide in the presence of anthraquinone-2-carboxylic acid under visible light irradiation.
Directed metalation?￡?cross-coupling strategies. Total syntheses of the alleged and the revised phenanthrene natural product gymnopusin
Wang, Xin,Fu, Jian-Min,Snieckus, Victor
, p. 2680 - 2694 (2013/03/13)
The total synthesis of gymnopusin (2) is described. The originally assigned structure for gymnopusin 1a was found to be incorrect by total synthesis using the Directed ortho-Metalation (DoM)?￡?Cross- Coupling?￡?Directed remote Metalation (DreM) sequence, a demonstrable key strategy for the regioselective construction of the 9-phenanthrol core. The revised structure of gymnopusin (2) was confirmed by synthesis by adopting the same strategy but involving a key remote anionic Fries-rearrangement step. Both routes highlight methodologies and concepts which may be of value in the regiocontrolled synthesis of phenanthrenoids specifically and in complex polycyclic aromatics in general. Copyright
Synthetic route discovery and introductory optimization of a novel process to idebenone
Tsoukala, Anna,Bjorsvik, Hans-Rene
experimental part, p. 673 - 680 (2011/12/01)
An environmentally benign, convenient, high yielding, and cost-effective synthesis leading to idebenone is disclosed. The synthesis includes a bromination process for the preparation of 2-bromo-3,4,5-trimethoxy-1- methylbenzene, a protocol for the Heck cross-coupling reaction using either thermal or microwave heating, olefin reduction by palladium catalyzed hydrogenation, and a green oxidation protocol with hydrogen peroxide as oxidant to achieve the benzoquinone framework. The total synthesis is composed of six steps that provide an overall yield of 20% that corresponds to a step yield of 76%.
A green and efficient synthesis of 1-chloromethyl -2,3,4,5-tetramethoxy6- methylbenzene
Wang, Jin,Yang, Jian,Yang, Bo,Hu, Xiao,Sun, Jia-Qiang,Yang, Tao
experimental part, p. 717 - 718 (2011/04/22)
The title compound, a key intermediate for preparing coenzyme Q analogues, was prepared in excellent yield by a reaction sequence starting from the commercially available 3,4,5-trlmethoxybenzadehyde via Wolff-Kishner reduction, selective bromination, methoxylation and Blanc chloromethylation reaction.
A novel simple and efficient bromination protocol for activated arenes
Tsoukala, Anna,Liguori, Lucia,Occhipinti, Giovanni,Bj?rsvik, Hans-Rene?
body text, p. 831 - 833 (2009/05/07)
An efficient, high yielding, and environmentally benign bromination using an alkali metal bromide as the bromine source is disclosed. Investigation of the protocol revealed that the method operates for activated arenes producing the corresponding monobrominated products in good to excellent yields.
