Potassium Iodide → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask (50 cc) equipped with a mechanical stirrer was charged with 5-amino-2-chloro-4-fluorophenol (1.03 g, 6.37 mmol), cyclopentyl bromide (1.32 g, 8.82 mmol), tetrabutylammonium bromide (152 mg, 0.47 mmol) and potassium iodide (300 mg, 1.81 mmol) to prepare a solution in toluene (5 mL). Subsequently, 40% sodium hydroxide in aqueous solution (5 mL) was added slowly and the mixture was stirred under heating at 80° C. for 4.5 h. After completion of the reaction, the reaction mixture was cooled to room temperature and water (10 mL) was added, followed by extraction with ethyl acetate (20 mL×3). The organic layers were combined, washed with water (10 mL) and saturated brine (10 mL) and dried with anhydrous magnesium sulfate. After the desiccant was removed, the solvent was distilled off under vacuum to give 4-chloro-5-cyclopentyloxy-2-fluoroaniline (1.45 g, 6.30 mmol; yield=99.0%).

Provenance & Evidence