反応 #5312

反応方程式

iodine

Oxetane

NH4Cl

4-bromo-1-fluorobenzene

magnesium

→

title compound

収率 51.6%

4-Flurobenzenepropanol

収率 51.6%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度at reflux overnight
3. 3
   抽出extracted with ER (2×150 ml)
4. 4
   乾燥dried (Na2SO4) extracts
5. 5
   その他were evaporated
6. 6
   その他The residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
7. 7
   洗浄eluting with ER- CX (1:5→1:3)
8. 8
   workup.DISTILLATIONThe resultant oil was further purified by distillation

実験手順

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.

出典