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

Author

Anders Lennartsson

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Maria Quant

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Kasper Moth-Poulsen

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Synlett

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

Vol. 26 11 1501-1504

Subject Categories

Polymer Chemistry

DOI

10.1055/s-0034-1380417

More information

Latest update

5/17/2018