Benzyl Alcohol → 3-benzyloxy-2-nitro-N-methylaniline

Participants

Reaction Steps

Benzyl alcohol (9.54 mL, 92.2 mmol), tetrabutyl ammonium bromide (1.49 g, 4.62 mmol), and potassium carbonate (7.64 g, 55.3 mmol) were added to a toluene solution (39 mL) of 3-fluoro-N-methyl-2-nitroaniline (7.84 g, 46.1 mmol), and the mixture was heated under reflux for 6 hours. The reaction solution was cooled, and water (39 mL) was added thereto, followed by toluene extraction. The resulting organic layer was washed with water, and the solvent was distilled off under reduced pressure, thereby obtaining 11.9 g of a red, powdery target compound (yield: 100%).

Provenance & Evidence