تفاعل #5312

معادلة التفاعل

iodine

Oxetane

NH4Cl

4-bromo-1-fluorobenzene

magnesium

→

title compound

المردود 51.6%

4-Flurobenzenepropanol

المردود 51.6%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةat reflux overnight
3. 3
   استخلاصextracted with ER (2×150 ml)
4. 4
   تجفيفdried (Na2SO4) extracts
5. 5
   أخرىwere evaporated
6. 6
   أخرىThe residual oil was purified by flash chromatography over silica gel (Merck 9285, 0.5 cm wide column)
7. 7
   غسيلeluting with ER- CX (1:5→1:3)
8. 8
   workup.DISTILLATIONThe resultant oil was further purified by distillation

الإجراء التجريبي

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.

المصدر