66693-87-6Relevant academic research and scientific papers
Derivatives of m-Guaiacol, Their Preparation and Their Uses
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Paragraph 0125; 0129; 0130, (2021/11/05)
The invention concerns derivatives of m-guaiacol, their preparation and their uses as biocides, in particular as antibacterials or disinfectants.
Synthesis method of 2-bromo-5-methoxyphenol
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Paragraph 0096-0099, (2019/10/22)
The invention discloses a synthesis method of 2-bromo-5-methoxyphenol. According to the synthesis method, 3-methoxyphenol is taken as a raw material, firstly, the 3-methoxyphenol reacts with a protection reagent such as tert-butyldimethylsilyl chloride, a
Synthesis of 2-arylbenzofuran-3-carbaldehydes: via an organocatalytic [3+2] annulation/oxidative aromatization reaction
Zhang, Huiwen,Ma, Chunmei,Zheng, Ziwei,Sun, Rengwei,Yu, Xinhong,Zhao, Jianhong
supporting information, p. 4935 - 4938 (2018/05/23)
A novel organocatalytic [3+2] annulation/oxidative aromatization reaction of enals with 2-halophenols or β-naphthols is reported. This process enables chemo- and regioselective access to 2-arylbenzofuran-3-carbaldehydes without the use of transition metals or strong oxidants. Preliminary mechanistic studies reveal that an unprecedented, organocatalytic, direct α-arylation pathway is involved.
Practical, mild and efficient electrophilic bromination of phenols by a new I(iii)-based reagent: The PIDA-AlBr3 system
Satkar, Yuvraj,Ramadoss, Velayudham,Nahide, Pradip D.,García-Medina, Ernesto,Juárez-Ornelas, Kevin A.,Alonso-Castro, Angel J.,Chávez-Rivera, Ruben,Jiménez-Halla, J. Oscar C.,Solorio-Alvarado, César R.
, p. 17806 - 17812 (2018/05/28)
A practical electrophilic bromination procedure for phenols and phenol-ethers was developed under efficient and very mild reaction conditions. A broad scope of arenes was investigated, including the benzimidazole and carbazole core as well as analgesics such as naproxen and paracetamol. The new I(iii)-based brominating reagent PhIOAcBr is operationally easy to prepare by mixing PIDA and AlBr3. Our DFT calculations suggest that this is likely the brominating active species, which is prepared in situ or isolated after centrifugation. Its stability at 4 °C after preparation was confirmed over a period of one month and no significant loss of its reactivity was observed. Additionally, the gram-scale bromination of 2-naphthol proceeds with excellent yields. Even for sterically hindered substrates, a moderately good reactivity is observed.
Visible-light photoredox catalysis enabled bromination of phenols and alkenes
Zhao, Yating,Li, Zhe,Yang, Chao,Lin, Run,Xia, Wujiong
, p. 622 - 627 (2014/04/17)
A mild and efficient methodology for the bromination of phenols and alkenes has been developed utilizing visible light-induced photoredox catalysis. The bromine was generated in situ from the oxidation of Br- by Ru(bpy)33+, both of which resulted from the oxidative quenching process.
A New Approach to Rapid Parallel Development of Four Neurokinin Antagonists. Part 4. Synthesis of ZD2249 Methoxy Sulfoxide
Bowden, Sharon A.,Nigel Burke,Gray, Fiona,McKown, Steven,Moseley, Jonathan D.,Moss, William O.,Murray, Paul M.,Welham, Matthew J.,Young, Maureen J.
, p. 33 - 44 (2013/09/04)
The manufacture of ZD2249 methoxy sulfoxide (1) using a new project approach is described. Research department processes were scaled up to 100 L if process safety and robustness were not compromised; other factors were treated according to the new approach. Using this strategy, we were able to manufacture a key intermediate on sufficient scale to support delivery of 1 kg quantities of bulk drug within 6 months of the start of lab work.
Bu3SnH mediated oxidative radical cyclisations: Synthesis of 6H-benzo[c]chromen-6-ones
Bowman, Russell,Mann, Emma,Parr, Jonathan
, p. 2991 - 2999 (2007/10/03)
Attempts to synthesise 6H-benzo[c]chromen-6-ones by Bu3SnH mediated cyclisation of o-(benzoyl)aryl radicals failed because of the preferred trans conformation of the ester. This problem was overcome by using cyclisation of o-(benzyloxy)aryl and o-[(aryloxy)methyl]aryl radicals to yield 6H-benzo[c]chromenes followed by oxidation to the 6H-benzo[c]chromen-6-ones. 3-Methoxy-6H-benzo[c]chromen-6-one 1, one of the main biologically active constituents of shilajit, a herbal medicine used in countries surrounding the Himalayan mountains, was synthesised using Bu3SnH mediated cyclisation of 1-benzyloxy-2,4-dibromo-5-methoxybenzene 31 to yield 3-methoxy-6H-benzo[c]chromene 25 followed by PCC oxidation of the 6-position. In order to avoid the problems of rearrangement, the aryl radical cyclisation must be designed such that whichever way the spirodienyl intermediate rearranges, the same product is obtained. For instance, the Bu3SnH mediated cyclisation of 1-iodo- and 1-bromo-2-(3-methoxy-phenyloxymethyl)benzenes 22 and 23 respectively gave both the isomers, 1-methoxy-6H-benzo[c]chromenes 24 and 3-methoxy-6H-benzo[c]chromenes 25 via rearrangement of the intermediate spirodienyl radical. The synthesised 6H-benzo[c]chromenes were oxidised in high yield to the corresponding 6H-benzo[c]chromen-6-ones. The mechanism of the 'oxidative' Bu3SnH mediated cyclisation is discussed.
Bromination of Phenols by Use of Benzyltrimethylammonium Tribromide
Kajigaeshi, Shoji,Kakinami, Takaaki,Tokiyama, Hajime,Hirakawa, Takahiro,Okamoto, Tsuyoshi
, p. 627 - 630 (2007/10/02)
The reaction of phenols with benzyltrimethylammonium tribromide in dichloromethane-methanol for 1 h at room temperature gave polybromophenols in good yields.
Halogenation Using Quaternary Ammonium Polyhalides. IV. Selective Bromination of Phenols by Use of Tetraalkylammonium Tribromides
Kajigaeshi, Shoji,Kakinami, Takaaki,Okamoto, Tsuyoshi,Nakamura, Hiroko,Fujikawa, Masahiro
, p. 4187 - 4189 (2007/10/02)
Reaction of phenols with calculated amounts of benzyltrimethylammonium tribromide or tetrabutylammonium tribromide in dichloromethane-methanol for 0.5-1 h under mild conditions gave, selectively, the objective mono-, di-, or tribromophenols in good yields.
