Uses
4-Bromobenzylamine hydrochloride is used to study the characteristics of C-terminal polyamine modification in the presence of protease and amine. Further, it is used to prepare 1-(4-Brombenzyl)-pyrrole by reacting with 2,5-dimethoxy-tetrahydro-furan.
Synthesis
General procedure: in a glove box, to a flame-dried GLC vial fitted with a magnetic stirring bar was added [3a] + [BArF4] (1.0 mol%) and Me2PhSiH(2a) (2.1 or 5.0 equivalents). The specified 4-bromobenzonitrile was added to the glove box (in case of solid material) or via a microsyringe outside the glove box. The resulting reaction mixture was kept at room temperature for the indicated time. Upon completion of the reaction, a mixture of cyclohexane and tert-butyl methyl ether (90:10) containing 4% Et3N (0.5 mL) was added to quench the reaction. The resulting solution was filtered through a diatomaceous earth pad coated with a small amount of silica gel, and a solution of cyclohexane and tert-butyl methyl ether (90:10) containing 4% Et3N (3-4 mL) was used as the eluent. The solvent was removed under reduced pressure and the residue was dissolved in Et2O (1 mL), followed by the addition of HCl (2M in Et2O, 1.0 mL, 2.0 mmol, 10 equiv). The resulting suspension was stirred for 1 h and filtered to give 4-bromobenzylamine hydrochloride as a white to yellow solid.
References
[1] Synlett, 2017, vol. 28, # 18, p. 2411 - 2414
[2] Tetrahedron, 2014, vol. 70, # 4, p. 975 - 983
[3] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7005 - 7007
[4] Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8809 - 8814
[5] ACS Catalysis, 2018, vol. 8, # 10, p. 9125 - 9130
