156808-76-3Relevant academic research and scientific papers
Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu 4 NBr
Bai, Ya,Che, Xin,Liu, Nian,Ning, Shulin,Shi, Lingling,Wang, Shutao,Wang, Siyu,Xiang, Jinbao,Xie, Wenxia
, p. 1313 - 1316 (2019)
Electrochemical regioselective bromination of electron-rich aromatic rings using stoichiometric tetrabutylammonium bromide (n Bu 4 NBr) has been accomplished under mild conditions. This protocol provides an environmentally friendly and simple way for the construction of C-Br bond in moderate to high yields with wide functional group tolerance.
Surfactant Control of the Ortho/Para Ratio in the Bromination of Anilines. 2.
Cerichelli, Giorgio,Mancini, Giovanna,Luchetti, Luciana
, p. 3797 - 3802 (1994)
We report the bromination of some N,N-disubstituted anilines (N-ethyl-N-methylaniline, N,N-diethylaniline, N-butyl-N-methylaniline, 1-phenylpyrrolidine, 1-phenylpiperidine) both in aqueous suspension of cetyltrimethylammonium tribromide (CTAB3) and in homogeneous solution (CHCl3).In the presence of surfactant we observed a regioselectivity different from that observed in homogeneous conditions.The regioselectivity seems to depend on the nature of the substituents on the nitrogen of the aniline as well as on the temperature.An explanation based on specific interactions between the aniline and the packed structure of the aggregate is proposed.
Synthesis of Halogenated Anilines by Treatment of N, N-Dialkylaniline N-Oxides with Thionyl Halides
Reed, Hayley,Paul, Tyler R.,Chain, William J.
, p. 11359 - 11368 (2018/08/06)
The special reactivity of N,N-dialkylaniline N-oxides allows practical and convenient access to electron-rich aryl halides. A complementary pair of reaction protocols allow for the selective para-bromination or ortho-chlorination of N,N-dialkylanilines in up to 69% isolated yield. The generation of a diverse array of halogenated anilines is made possible by a temporary oxidation level increase of N,N-dialkylanilines to the corresponding N,N-dialkylaniline N-oxides and the excision of the resultant weak N-O bond via treatment with thionyl bromide or thionyl chloride at low temperature.
