Reacción #337359

Ecuación de reacción

ethyl 4-bromobenzoate

ethylmagnesium bromide

Et2O

→

3-(4-bromophenyl)-pentan-3-ol

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction mixture was removed from the ice-bath
2. 2
   OtroAfter 18 h the opaque mixture was quenched with satd ammonium chloride (50 mL)
3. 3
   Extracciónextracted with Et2O (2×50 mL)
4. 4
   LavadoThe combined extracts were washed with brine
5. 5
   Secadodried (anhyd Na2SO4)
6. 6
   Concentraciónconcentrated under reduced pressure

Procedimiento

A solution of ethyl 4-bromobenzoate (1.6 mL, 10 mmol) in anhyd THF (50 mL) was chilled to 0° C. and then charged dropwise with a 3.0 M solution of ethylmagnesium bromide in Et2O (7.0 mL, 21 mmol). After 15 min, the reaction mixture was removed from the ice-bath and stirred at ambient temperature. After 18 h the opaque mixture was quenched with satd ammonium chloride (50 mL) and extracted with Et2O (2×50 mL). The combined extracts were washed with brine, dried (anhyd Na2SO4) and concentrated under reduced pressure to give 3-(4-bromophenyl)-pentan-3-ol (2.45 g, quant) as a colorless liquid, which was used without purification in the next step: 1H-NMR (CDCl3) δ 7.46 (2H, d, J=8.3), 7.26 (2.3H, d, J=8.3), 1.78-1.86 (4H, overlapping quartets, J=7), 0.76 (6H, t, J=7.3).

Fuente