Reacción #5312

Ecuación de reacción

iodine

Oxetane

NH4Cl

4-bromo-1-fluorobenzene

magnesium

→

title compound

Rendimiento 51.6%

4-Flurobenzenepropanol

Rendimiento 51.6%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe reaction mixture was heated
2. 2
   Temperaturaat reflux overnight
3. 3
   Extracciónextracted with ER (2×150 ml)
4. 4
   Secadodried (Na2SO4) extracts
5. 5
   Otrowere evaporated
6. 6
   OtroThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
7. 7
   Lavadoeluting with ER- CX (1:5→1:3)
8. 8
   workup.DISTILLATIONThe resultant oil was further purified by distillation

Procedimiento

A Grignard reagent was prepared from 4-bromo-1-fluorobenzene (8.0 g)., magnesium turnings (1.10 g), and iodine (one small crystal) in THF (40 ml). Oxetane (2.3 g) in THF (10 ml) was added at RT and the reaction mixture was heated at reflux overnight. The cooled solution was poured into aqueous saturated NH4Cl (100 ml), extracted with ER (2×150 ml) and the combined, dried (Na2SO4) extracts were evaporated. The residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column), eluting with ER- CX (1:5→1:3). The resultant oil was further purified by distillation to give the title compound (3.15 g) as a colourless oil, b.p. 150°/0.8 torr.

Fuente