Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using nBu4NBr

Wenxia Xie; Shulin Ning; Nian Liu; Ya Bai; Shutao Wang; Siyu Wang; Lingling Shi; Xin Che; Jinbao Xiang

doi:10.1055/s-0037-1611545

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(11): 1313-1316
DOI: 10.1055/s-0037-1611545

letter

Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using ⁿ Bu₄NBr

Wenxia Xie

,

Shulin Ning

,

Nian Liu

,

Ya Bai

,

Shutao Wang

,

Siyu Wang

,

Lingling Shi

,

Xin Che

,

Jinbao Xiang*

The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Road, Changchun, Jilin 130021, P. R. of China eMail: jbxiang@jlu.edu.cn

› Institutsangaben

Abstract

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Abstract

Electrochemical regioselective bromination of electron-rich aromatic rings using stoichiometric tetrabutylammonium bromide ( ⁿ Bu₄NBr) 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.

Key words

electrochemistry - regioselective - bromination - aromatic ring - stoichiometric - tetrabutylammonium bromide

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Referenzen

References and Notes

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18 4-Bromo-N,N-dimethylaniline (2a) – Typical Procedure A 10 mL distillation flask equipped with a magnetic stir bar was charged with N,N-dimethylaniline (1a, 0.25 mmol), CH₂Cl₂ (5 mL), and ⁿ Bu₄NBr (0.375 mmol). The resulting suspension was stirred until complete dissolution. The flask equipped with graphite rod anode (d = 5 mm) and graphite rod cathode (d = 5 mm). The reaction mixture was stirred and electrolyzed at a constant current of 5 mA under room temperature for 3.5 h. The reaction mixture was diluted with CH₂Cl₂ (15 mL), washed successively with water (10 mL) and brine (10 mL), dried over Na₂SO₄, and concentrated in vacuo. Purification by flash column chromatography (silica gel, petroleum ether–dichloromethane 3:1) afforded the desired product 2a (80% yield) as a white solid; mp 54–55 °C. ¹H NMR (300 MHz, CDCl₃): δ = 7.34–7.25 (m, 2 H), 6.60 (d, J = 9.0 Hz, 2 H), 2.93 (s, 6 H). ¹³C NMR (75 MHz, CDCl₃): δ = 149.5, 131.6, 114.1, 108.5, 40.5.
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Supporting Information

Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using n Bu4NBr

Electrochemical Regioselective Bromination of Electron-Rich Aromatic Rings Using ⁿ Bu₄NBr