Triethylamine → 3-Bromo N (2 (2 (2 methoxyethoxy)ethoxy)ethyl)-5-nitrobenzamide

Participants

Reaction Steps

T3P, 50 wt % in EtOAc (25 mL, 42.0 mmol) was slowly added to a solution of 3-bromo-5-nitrobenzoic acid (7.05 g, 28.7 mmol), 2-(2-(2-methoxyethoxy)ethoxy)ethanamine (4 g, 24.25 mmol) and Et3N (12 mL, 86 mmol) in EtOAc (50 mL) whilst immersed in an ice-bath. Once the addition was complete, the ice bath was removed and the reaction allowed to stir at rt for 2 h. The mixture was partitioned between sat. aq. NaHCO3 solution (100 mL) and EtOAc (100 mL). The organic layer was washed with aq K2CO3 solution (10 g in 100 mL) and brine (100 mL), before being dried (MgSO4), filtered and concentrated in vacuo to afford the sub-title compound (8.23 g) as a brown oil.

Provenance & Evidence