Water → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask (50 cc) was charged with bis(5-amino-2-chloro-4-fluorophenyl)carbonate (1.51 g, 4.34 mmol), cyclopentyl methanesulfonate (1.51 g, 9.21 mmol) and tetrabutylammonium bromide (70 mg, 0.22 mmol) to prepare a solution in toluene (8 mL). Subsequently, 48% sodium hydroxide in aqueous solution (4 mL) was added slowly and the mixture was stirred under heating at 80° C. for 1 h. Subsequently, 48% sodium hydroxide in aqueous solution (4 mL) was added slowly and the mixture was stirred under heating at 80° C. for an additional 1 h. After completion of the reaction, the reaction mixture was cooled to room temperature and water (15 mL) was added, followed by extraction with toluene (10 mL×2). The organic layers were combined and washed with water (10 mL×2). The solvent was distilled off under vacuum from the resulting toluene solution, thereby giving 4-chloro-5-cyclopentyloxy-2-fluoroaniline (1.92 g, 8.36 mmol; yield=96.4%; purity on HPLC=94.4%).

Provenance & Evidence