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

Temperature

80 °C

2-Chloro-4-fluoro-5-aminophenol (1.02 g, 6.28 mmol), potassium carbonate (1.72 g, 12.4 mmol), potassium iodide (4.0 mg, 0.024 mmol) and N,N-dimethylformamide (5 ml) as a solvent were placed in a two-necked round bottom flask (25 cc) and stirred at 80° C. for one hour. Then, cyclopentyl bromide (1.00 g, 6.71 mmol) was added thereto, followed by stirring at 80° C. for further 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature, water (20 ml) was added thereto, and the mixuture was extracted with toluene (20 ml×3 portions). The organic layers were combined, washed with water (10 ml) and a saturated aqueous sodium chloride solution (10 ml) and dried over magnesium sulfate. After removing the drying agent, the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxyaniline (1.43 g, 6.23 mmol, 99.0% yield). Boiling point: 143°-145° C./1.5 mmHg.

1. stirringby stirring at 80° C. for further 2 hours
2. customAfter completion of the reaction
3. temperaturethe reaction solution was cooled to room temperature
4. extractionthe mixuture was extracted with toluene (20 ml×3 portions)
5. washwashed with water (10 ml)
6. dry with materiala saturated aqueous sodium chloride solution (10 ml) and dried over magnesium sulfate
7. customAfter removing the drying agent
8. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-dbdfb2611cd4413789eee9efa790407b

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05554581