TY - JOUR AU - Barraza, Scott J.; Denmark, Scott E. TI - Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions SN - 0936-5214 SN - 1437-2096 PY - 2017 JO - Synlett JF - Synlett LA - EN VL - 28 IS - 20 SP - 2891 EP - 2895 ET - 2017/08/21 DA - 2017/12/06 KW - bromoaniline KW - alkylation KW - rearrangement KW - bromine AB - Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1590882 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1590882 ER -