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A Convenient Route to 2-Bromo-3-chloronorbornadiene and 2,3-Dibromonorbornadiene

Anders Lennartson (Institutionen för kemi och kemiteknik, Polymerteknologi) ; Maria Quant (Institutionen för kemi och kemiteknik, Polymerteknologi) ; Kasper Moth-Poulsen (Institutionen för kemi och kemiteknik, Polymerteknologi)
Synlett : Accounts and Rapid Communications in Synthetic Organic Chemistry (0936-5214). Vol. 26 (2015), 11, p. 1501-1504.
[Artikel, refereegranskad vetenskaplig]

Substituted norbornadienes are useful in a wide range of applications, including molecular solar-thermal (MOST) energy storage systems. An important precursor for 2,3-substituted norbornadienes is 2-bromo-3-chloronorbornadiene, where the two halogen atoms can be substituted selectively through two consecutive Suzuki cross-coupling reactions. Previous routes to 2-bromo-3-chloronorbornadiene have used 1,2-dibromoethane as a brominating agent, a substance known to be carcinogenic and the use of which is restricted in certain countries. Herein is reported a one-pot route to 2-bromo-3-chloronorbornadiene in 50% yield using p-toluenesulfonyl bromide as a bromine source. In addition, the procedure has been adapted to allow synthesis of 2,3-dibromonorbornadiene in 37% yield.

Nyckelord: alkenes, bromine, chlorine, organometallic reagents, regioselectivity

Denna post skapades 2015-07-06. Senast ändrad 2015-07-20.
CPL Pubid: 219456


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Institutionen för kemi och kemiteknik, Polymerteknologi



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