Benzyl Alcohol → HCID 67954029, compound

Participants

Reaction Conditions

Reaction Steps

An aqueous solution of 70% ethyl amine (25 mL, 0.315 mol) was added dropwise to a toluene solution (167 mL) of 2,4-difluoronitrobenzene (16.7 g, 0.105 mol) 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. The resulting organic layer was concentrated under reduced pressure until reduced to about half (the concentrated solution including a crude product of 5-fluoro-N-ethyl-2-nitroaniline). Benzyl alcohol (21.7 mL, 0.21 mol), tetrabutyl ammonium hydrogen sulfate (3.56 g, 0.01 mmol), potassium carbonate (21.76 g, 0.157 mol), and water (1.7 mL) were added to the resulting solution, and the mixture was heated under reflux for 3 hours. The reaction solution was cooled, and water (84 mL) was added thereto. Thereafter, the mixture was stirred at 70° C. for 1 hour, and stirred under ice cooling for 30 minutes. Next, precipitated crystals were collected by filtration, and the resulting crystals were washed with water, and dried at 50° C., thereby obtaining 17.7 g of a yellow, powdery target compound (yield: 62%).

Provenance & Evidence