Cesium carbonate → 4-(2-Fluoro-4-nitrophenyl)morpholin-3-one

Participants

Reaction Conditions

Reaction Steps

3,4-Difluoro-1-nitrobenzene (0.50 mL, 4.52 mmol) was dissolved in 8 mL NMP. To it was added morpholin-3-one (0.91 g, 9.04 mmol) and cesium carbonate (2.95 g, 9.04 mmol). The mixture was stirred at 120° C. for 6 h. It was cooled to RT, diluted with 200 mL EtOAc, washed with brine three times, dried, concentrated in vacuo and subjected to silica flash column (0-30% EtOAc in DCM) to isolate 4-(2-fluoro-4-nitrophenyl)morpholin-3-one (580 mg, 53%). It was dissolved in 200 mL EtOAc and 100 mL MeOH. To it was added 500 mg 10% Pd/C. The mixture was stirred under a hydrogen balloon for overnight. The mixture was filtered through celite, and the solid cake was thoroughly washed with MeOH. The filtrate was concentrated in vacuo to afford 4-(4-amino-2-fluorophenyl)morpholin-3-one in quantitative yield.

Provenance & Evidence