Uses
2-Bromomesitylene is a useful synthetic intermediate, Aromatics, Boron Derivatives, Catalyst. It is an intermediate used to prepare Hydrogen[4-[bis(2,4,6-trimethylphenyl)phosphino]-2,3,5,6-tetrafluorophenyl]hydrobis(2,3,4,5,6-pentafluorophenyl)borate (H714510) which is a frustrated phosphonium borate for metal-free catalytic hydrogenation of imines.
Synthesis
The general procedure for the synthesis of 2-bromo-1,3,5-trimethylbenzene from 1,3,5-trimethylbenzene was as follows: N-bromosuccinimide (NBS, 1.0 mmol) and Catalyst 1 (0.1 or 1 mol% Au based on the substrate) were accurately weighed and added to 10 mL of a sealed reaction vessel, followed by 1,2-dichloroethane (DCE, 2 mL) and 1,3,5- trimethylbenzene (1.0 mmol). The reaction mixture was stirred at a set temperature for a specified time. Upon completion of the reaction, the catalyst was removed by separation using a magnet, followed by concentration of the reaction solution under reduced pressure and final purification by column chromatography to afford the target product 2-bromo-1,3,5-trimethylbenzene.
References
[1] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[2] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 11, p. 2028 - 2032
[4] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1063 - 1066
[5] Synthesis, 2002, # 2, p. 169 - 171
