Sodium Hydroxide → 4-Chloro-5-(cyclopentyloxy)-2-fluorobenzenamine

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Ethyl alcohol (50 ml) and a 2N aqueous solution of sodium hydroxide (100 ml) were added to the thus-obtained ethyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate, followed by stirring for 4 hours while heating in an oil bath at 110° C. After completion of the reaction, the solvent was distilled off, and the residue was extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with a saturated aqueous sodium chloride, dried, and the solvent was distilled off under reduced pressure to obtain 2-fluoro-4-chloro-5-cyclopentyloxyaniline (9.36 g, 40.8 mmol, 97% yield). 1H-NMR Spectrum (CDCl3, TMS, ppm): δ1.40-2.07 (8H, m), 3.72 (2H, br s), 4.57 (1H, m), 6.35 (1H, d, JHF =8.0 Hz), 6.98 (1H, d, JHF =10.5 Hz). IR Spectrum (KBr, disk, cm-1): 2980, 1635, 1510, 1423, 1250, 1190.

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