p-Aminophenylacetic acid ethyl ester → HCID 67021331, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-4-fluoro-3-nitrobenzene (MATRIX SCIENTIFIC) (10.7 g, 48.7 mmol) and 4-aminophenylacetic acid ethyl ester (8.7 g, 48.7 mmol) in NMP (50 mL) is stirred for 48 h at 110° C. The reaction mixture is allowed to cool at rt, diluted with EtOAc and H2O. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed brine, dried (Na2SO4), filtered and concentrated. Silica gel column chromatography purification (Hexane/EtOAc, 4:1) of the crude product affords the title compound as an orange oil: ES-MS: 380.9 [M+2]+; single peak at tR=5.75 min (System 1); Rf=0.27 (Hexane/EtOAc, 4:1).

Provenance & Evidence