Diisopropylethylamine → (3-Bromo-2-nitro-phenylamino)-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-3-fluoro-2-nitrobenzene (10.25 g, 46.6 mmol; Ark Pharm, Inc., Libertyville, Ill.), ethyl 2-aminoacetate hydrochloride (6.50 g, 46.6 mmol; Aldrich), and N-ethyl-N-isopropylpropan-2-amine (24.35 ml, 140 mmol) in DMA (116 ml) was heated to 80° C. for 5 h. The mixture was diluted with DCM (400 ml), added to a separatory funnel, and washed with water (4×200 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give ethyl 2-((3-bromo-2-nitrophenyl)amino)acetate (210b, >99% yield) as a yellow oil (contaminated with DMA). MS (ESI, pos. ion) m/z: 303.0/305.0 (M+1).

Provenance & Evidence