Реакция #570650

Уравнение реакции

Oxetane

NH4Cl

4-bromo-1-fluorobenzene

magnesium

iodine

→

title compound

Выход 51.6%

4-Fluorobenzenepropanol

Выход 51.6%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated
2. 2
   Температураat reflux overnight
3. 3
   Экстракцияextracted with ER (2×150 ml)
4. 4
   Сушкаdried (Na2SO4) extracts
5. 5
   Другоеwere evaporated
6. 6
   ДругоеThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 5.0 cm wide column)
7. 7
   Промывкаeluting with ER-CX (1:5→1:3)
8. 8
   workup.DISTILLATIONThe resultant oil was further purified by distillation

Методика

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, 5.0 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.

Источник