84492-02-4Relevant academic research and scientific papers
Synthesis of 2-bromomethyl-2,3-dihydrobenzofurans from 2-allylphenols enabled by organocatalytic activation of: N -bromosuccinimide
Furst, Carolina G.,Cota, Paulo H. P.,Dos Santos Wanderley, Taciano A.,Alberto, Eduardo E.
, p. 15677 - 15684 (2020/10/22)
2-Bromomethyl-2,3-dihydrobenzofurans are valuable and highly functionalized compounds that can be obtained by an intramolecular reaction between 2-allylphenols and a bromenium ion source (Br+). Due to the ineffectiveness of the safe and easy-to-handle brominating agent N-bromosuccinimide (NBS) to deliver the desired products, a catalytic process using a mixture of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and acetic acid was conceived. We hypothesized that this catalytic system delivers in situ acetyl hypobromite (AcOBr) as the active brominating agent, enabling the conversion of a range of 2-allylphenols with diverse electron densities to the products. The protocol was robust enough to permit the reaction to be scaled up to 10 mmols of starting material. Besides, the functional group interconversion with a 2-bromomethyl-2,3-dihydrobenzofuran derivative was successfully demonstrated. This journal is
1,3-dibromo-5,5-dimethylhydantoin, a useful reagent for aromatic bromination
Chassaing, Christophe,Haudrechy, Arnaud,Langlois, Yves
, p. 4415 - 4416 (2007/10/03)
1,3-dibromo-5,5-dimethylhydantoin (DBDMH) is a useful and easy to handle reagent for bromination of various aromatic derivatives substituted with electron donating groups. In the presence of trimethylsilyltrifluoromethanesulfonate, DBDMH showed increased reactivity, and in one case, the reaction followed another pathway, suggesting an alternative mechanism.
Phase-transfer catalyzed nucleophilic addition of arylalkanenitrile carbanions to substituted propenylarenes
Lasek,Makosza
, p. 780 - 782 (2007/10/02)
Phenylacetonitrile and 2-phenylalkanenitriles react under phase transfer catalysis conditions with 2-propenylanisoles containing electron-withdrawing substituents (or their corresponding precursors, 2-allylanisoles) via the Michael addition pathway to give substituted 4-aryl-2-phenylbutyronitriles.
