Reacción #158516

Ecuación de reacción

3-nitrophenol

K2CO3

ethyl bromoacetate

→

ethyl 4-nitrophenoxyacetate

Rendimiento 92.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA dry reaction flask
2. 2
   Otroequipped with a reflux condenser, N2 inlet and a magnetic stirring bar
3. 3
   TemperaturaThe reaction mixture was refluxed for 16 h
4. 4
   Temperaturacooled
5. 5
   ExtracciónThe resulting aqueous solution was extracted with CH2Cl2 (3×500 mL)
6. 6
   Secadodried over anhydrous Na2SO4 and solvent
7. 7
   Otrowas removed

Procedimiento

A dry reaction flask equipped with a reflux condenser, N2 inlet and a magnetic stirring bar was charged with 3-nitrophenol (76.45 g, 550 mmol), K2CO3 (76.45 g, 550 mmol) and dry acetone (500 mL) under N2 atmosphere. To this at room temperature was added ethyl bromoacetate (55.44 mL, 500 mmol) over a period of 15 min. The reaction mixture was refluxed for 16 h, cooled and poured over ice-water (4 Kg). The resulting aqueous solution was extracted with CH2Cl2 (3×500 mL), dried over anhydrous Na2SO4 and solvent was removed to obtain 103 g (92%) of the desired ethyl 4-nitrophenoxyacetate. 1H NMR (CDCl3): δ 8.20 (d, 2H, J=8.2 Hz), 6.95 (d, 2H, J=8.1 Hz), 4.72 (s, 2H), 4.25 (q, 2H), 1.23 (t, 3H); LCMS: ret. time: 27.07 min.; purity: 100%; MS: 267 (M+acetonitrile).

Fuente