Reacción #217902

Ecuación de reacción

water

compound

Benzyl-[2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

K2CO3

2-chloro-4-fluoro-benzonitrile

→

title compound

Rendimiento 95.8%

Benzyl-{2-[4-(3-chloro-4-cyano-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Rendimiento 95.8%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónExtract the aqueous layer with EtOAc
2. 2
   SecadoDry the organic layer over Na2SO4
3. 3
   OtroPurify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85)

Procedimiento

Combine the compound from Example 218 step 2 (692 mg, 2.12 mmol) and K2CO3 (323 mg, 2.33 mmol) in DMF (9 mL), stir the mixture at room temperature for 30 min and then add 2-chloro-4-fluoro-benzonitrile (330 mg, 2.12 mmol), and heat at 100° C. overnight. Cool to ambient temperature and pour into water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Purify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85) to obtain the title compound (940 mg, 95%). Electrospray MS M−1 ion=461, 1H-NMR (CDCl3, 400 MHz): 7.57 (d, 1H, J=7.8 Hz), 7.36-7.13 (m, 7H), 7.00-6.85 (m, 4H), 4.44-4.36 (m, 2H), 3.49-3.32 (m, 2H), 2.83-2.73 (m, 2H), 1.51-1.43 (m, 9H).

Fuente