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

Participants

Reaction Conditions

Reaction Steps

A two-necked, round-bottomed flask (25 cc) was charged with 5-amino-2-chloro-4-fluorophenol (1.015 g, 6.28 mmol), potassium carbonate (1.72 g, 12.4 mmol), potassium iodide (4.0 mg, 0.024 mmol) and solvent N,N-dimethylformamide (5 mL) and the mixture was stirred at 80° C. for 1 h. Subsequently, cyclopentyl bromide (1.00 g, 6.71 mmol) was added and the mixture was stirred at 80° C. for an additional 2 h. After the reaction was completed, the reaction mixture was cooled to room temperature and water (20 mL) was added, followed by extraction with toluene (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 (1.43 g, 6.23 mmol; yield=99.0%). BP: 143°-145° C./1.5 mmHg 1H-NMR(CDCl3, TMS,ppm): δ1.40-2.00(8H,m), 3.72(2H,s), 4.67(1H,m), 6.39(1H,d,JHF =9.0Hz), 7.04(1H,d,JHF =11.0Hz). IR (neat, cm-1): 3500, 3400, 1630, 1510, 1420, 1245, 1185.

Provenance & Evidence