Potassium Iodide → 2-Fluoro-4-chloro-5-(3-methylcyclopentyl)oxyaniline

Temperature

100 °C

A round-bottomed flask (200 cc) equipped with a mechanical stirrer was charged with 5-amino-2-chloro-4-fluorophenol (3.00 g, 18.6 mmol), 3-methylcyclopentyl p-toluenesulfonate (4.60 g, 18.6 mmol), tetrabutylammonium bromide (300 mg, 0.93 mmol) and potassium iodide (300 mg, 1.81 mmol) to prepare a solution in toluene (30 mL). Subsequently, 48% sodium hydroxide in aqueous solution (30 mL) was added slowly and the mixture was stirred under heating at 100° C. for 48 h. After completion of the reaction, the reaction mixture was cooled to room temperature and water (50 mL) was added, followed by extraction with ethyl acetate (30 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 2-fluoro-4-chloro-5-(3-methylcyclopentyloxy)aniline (1.94 g, 7.96 mmol; yield=42.9%) as a brown oil. 1H-NMR(CDCl3,TMS,ppm): δ1.02 and 1.10(total 3H, each d,J=6.0Hz), 1.22-2.58(7H,m), 3.75(2H,brs), 4.65(1H,m), 6.33(1H,d,JHF =8.0Hz), 6.98(1H,d,JHF =10.0Hz)

1. customA round-bottomed flask (200 cc) equipped with a mechanical stirrer
2. customAfter completion of the reaction
3. temperaturethe reaction mixture was cooled to room temperature
4. extractionfollowed by extraction with ethyl acetate (30 mL×3)
5. washwashed with water (10 mL) and saturated brine (10 mL)
6. dry with materialdried with anhydrous magnesium sulfate
7. customAfter the desiccant was removed
8. distillationthe solvent was distilled off under vacuum

ORD record

ord-612bd0831ddb4691bee967cf2f4d32a5

Source dataset

uspto-grants-1997_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05639915