Reaktion #5312

Reaktionsgleichung

iodine

Oxetane

NH4Cl

4-bromo-1-fluorobenzene

magnesium

→

title compound

Ausbeute 51.6%

4-Flurobenzenepropanol

Ausbeute 51.6%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture was heated
2. 2
   Temperaturat reflux overnight
3. 3
   Extraktionextracted with ER (2×150 ml)
4. 4
   Trocknendried (Na2SO4) extracts
5. 5
   Sonstigewere evaporated
6. 6
   SonstigeThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
7. 7
   Wascheneluting with ER- CX (1:5→1:3)
8. 8
   workup.DISTILLATIONThe resultant oil was further purified by distillation

Vorschrift

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.

Quelle