Hydrochloric Acid → benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate

Participants

Reaction Steps

Then, benzyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (12.2 g, 41.3 mmol), potassium carbonate (5.97 g, 432.1 mmol), cyclopentyl p-toluenesulfonate (11.2 g, 46.4 mmol) and acetone (150 ml) as a solvent were charged into a 500 cc round-bottom Flask and heated for 9 hours while refluxing. After completion of the reaction, the reaction mixture was poured into 1N hydrochloric acid. After thoroughly stirring, the precipitated benzyl N-(2-fluoro-4-chloro-5-cyclopentyloxyphenyl)carbamate as a pale yellow solid (14.9 g, 40.9 mmol, 994 yield) was isolated by filtration and well dried. 1H-NMR Spectrum (CDCl3, TMS, ppm): δ1.48-2.07 (8H, m), 4.83 (1H, m), 5.26 (2H, s), 6 92 (1H, br, s) 7.14 (1H, d, JHF =11.5 Hz), 7.47 (5H, s), 7.93 (1H, d, JHF =8.3 Hz).

Provenance & Evidence