Reacción #333538

Ecuación de reacción

NaOH

KOH

3-chloro-phenol

4-fluoro-2-methyl-1-nitro-benzene

→

4-(3-chloro-phenoxy)-2-methyl-1-nitro-benzene

Rendimiento 47.1%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled to 25° C.
2. 2
   TemperaturaThis mixture was then heated to 130° C. for 12 h
3. 3
   Extracciónextracted with EtOAc (3×25 mL)
4. 4
   LavadoThe organic phase was washed with brine (3×5 mL)
5. 5
   Secadodried over sodium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by column chromatography (silica, 0.5% EtOAc in hexanes)

Procedimiento

To a suspension of 3-chloro-phenol (1.65 g, 12.89 mmol) in DMF (10 mL), was added KOH (1.45 g, 25.78 mmol) and the mixture heated at 110° C. for 30 min. The mixture was cooled to 25° C. and 4-fluoro-2-methyl-1-nitro-benzene (0.5 g, 3.22 mmol) was added. This mixture was then heated to 130° C. for 12 h. The reaction mixture was treated with 10% NaOH solution and extracted with EtOAc (3×25 mL). The organic phase was washed with brine (3×5 mL), dried over sodium sulfate and concentrated. The residue was purified by column chromatography (silica, 0.5% EtOAc in hexanes) to afford 4-(3-chloro-phenoxy)-2-methyl-1-nitro-benzene (400 mg, 47%). MS (M+H)+=263; 1H NMR (CDCl3) δ: 8.05 (d, J=7.1 Hz, 1H), 7.33 (t, J=6.0 Hz, 1H), 7.20 (d, J=5.3 Hz, 1H), 7.06 (s, 1H), 7.03-6.85 (m, 3H), 2.59 (s, 3H).

Fuente