A Convenient Route to 2-Bromo-3-chloronorbornadiene and 2,3-Dibromonorbornadiene
Artikel i vetenskaplig tidskrift, 2015

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.

alkenes

organometallic reagents

bromine

chlorine

regioselectivity

Författare

Anders Lennartsson

Chalmers, Kemi och kemiteknik, Tillämpad kemi, Polymerteknologi

Maria Quant

Chalmers, Kemi och kemiteknik, Tillämpad kemi, Polymerteknologi

Kasper Moth-Poulsen

Chalmers, Kemi och kemiteknik, Tillämpad kemi, Polymerteknologi

Synlett

0936-5214 (ISSN) 1437-2096 (eISSN)

Vol. 26 11 1501-1504

Ämneskategorier

Polymerkemi

DOI

10.1055/s-0034-1380417

Mer information

Senast uppdaterat

2018-05-17