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Synlett 2020; 31(15): 1523-1526
DOI: 10.1055/s-0040-1707199
DOI: 10.1055/s-0040-1707199
letter
Facile Synthesis of β-Bromostyrenes by Direct Bromination of Styrenes with N-Bromosuccinimide and Sodium Persulfate
This work was supported by the National Natural Science Foundation of China (Nos. 21801065 and U180425).Further Information
Publication History
Received: 23 May 2020
Accepted after revision: 11 June 2020
Publication Date:
27 July 2020 (online)
Abstract
A new, direct, efficient, and transition-metal-free method is reported for the synthesis of β-bromostyrenes from styrenes by using N-bromosuccinimide as the brominating reagent and sodium persulfate (Na2S2O8) as the oxidant. This convenient and concise reaction is practical, operationally simple, and can be adapted for large-scale syntheses.
Key words
bromination - styrenes - bromosuccinimide - green chemistry - sodium persulfate - bromostyrenesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707199.
- Supporting Information
Primary Data
- Primary Data
for this article are available online at https://doi.org/10.1055/s-0040-1707199 and can be cited using the following DOI: 10.4125/pd0119th.
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(2-Bromovinyl)benzene (2a); Typical Procedure
Styrene (1a; 2.0 mmol, 1.0 equiv) was added to a solution of NBS (2.1 mmol, 1.05 equiv) and Na2S2O8 (4.0 mmol, 2.0 equiv) in DCE (3 mL) in a sealed tube. The mixture was warmed to 100 °C and stirred for 3 h. When the reaction was complete, the mixture was purified directly by flash chromatography (silica gel, petroleum ether) to give a white oil; yield: 230.5 mg (63%, E/Z = 10:1).
1H NMR (400 MHz, CDCl3): δ = 7.31–7.27 (m, 5 H), 7.09 (d, J = 14.0 Hz, 1 H), 6.75 (d, J = 14.0 Hz, 1 H).