3-Iodobenzyl bromide → HCID 89559790, compound

Participants

Reaction Conditions

Reaction Steps

3-Iodobenzyl bromide (14.4 g, 48.6 mmol) was added to a RT solution of rac-ethyl 2-((2,2-dimethylpropylidene)amino)propanoate (10 g, 48.6 mmol) from above in toluene (100 mL) under argon and the resulting mixture was cooled to −10° C. before KOtBu (10.9 g, 97.2 mmol) was added portionwise. The reaction mixture was stirred at 0° C. for 4 h before being quenched with water. The toluene was evaporated in vacuo and the remaining aqueous phase was extracted with EtOAC (3×). The combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo. The residue was stirred in 1M aq. HCl overnight after which LCMS showed the desired product. EtOAc was added and the mixture was stirred for 30 min before the layers were separated. The organic phase was discarded and the aqueous phase was basified with 2M aq. NaOH and re-extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and evaporated in vacuo to give the title compound that was used further without purification. LC-MS D: tR=0.88 min; [M+H+MeCN]+=375.06.

Provenance & Evidence