Cesium carbonate → HCID 86657976, compound

Participants

Reaction Steps

To a solution of benzyl (3-hydroxy-4-methylphenyl)carbamate (83.1 g, 321 mmol) in N,N-dimethylformamide (300 mL) were added cesium carbonate (157 g, 482 mmol) and 2-chloro-5-nitropyridine (50.9 g, 321 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (1 L), and the obtained aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layer was washed with saturated brine (100 mL) and purified by basic silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate/hexane (1:1) to give the title compound (91.8 g, 75%) as a pale-yellow solid.

Provenance & Evidence