Benzyl Alcohol → 5-benzyloxy-N-methyl-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

An aqueous solution of 40% methyl amine (8.2 mL, 94.2 mmol) was added dropwise to a toluene solution (50 mL) of 2,4-difluoronitrobenzene (5.0 g, 31.4 mmol) under ice cooling, and the mixture was stirred at 35-40° C. for 2 hours. Water was added to the reaction solution, and toluene extraction was performed, followed by washing with water. Benzyl alcohol (6.5 mL, 62.8 mmol), tetrabutyl ammonium bromide (1.0 g, 3.1 mmol) and potassium carbonate (5.2 g, 37.6 mmol) were added to the resulting organic layer, and the mixture was heated under reflux for 4 hours. After the reaction solution was cooled, water (25 mL) was added, and the mixture was stirred at 70° C. for 1 hour. The mixture was stirred under ice cooling for 30 minutes, and precipitated crystals were collected by filtration. The resulting crystals were washed with water and dried at 50° C., thereby obtaining 7.8 g of orange, powdery 5-benzyloxy-N-methyl-2-nitroaniline (yield: 96%).

Provenance & Evidence