반응 #600878

반응 방정식

5-bromo-2-fluorobenzaldehyde

ethane-1,2-diol

p-toluenesulfonic acid

→

title compound

수율 77.2%

2-(5-Bromo-2-fluoro-phenyl)-[1,3]dioxolane

수율 77.2%

용매

toluene

반응 조건

후처리

1. 1
   기타To a 3 neck round bottom flask, fitted with a Dean-Stark apparatus
2. 2
   온도heated
3. 3
   온도under reflux for 18 h
4. 4
   온도After cooling
5. 5
   농축the mixture was concentrated in vacuo
6. 6
   workup.ADDITIONThe residue was diluted with EtOAc (50 ml)
7. 7
   세척the organic phase was washed with sat. NaHCO3 solution (30 ml), brine (30 ml)
8. 8
   건조dried (Na2SO4)
9. 9
   농축concentrated in vacuo
10. 10
    기타The crude residue was purified by column chromatography with heptane/EtOAc (95:5) as the eluent

실험 절차

To a 3 neck round bottom flask, fitted with a Dean-Stark apparatus, was added 5-bromo-2-fluorobenzaldehyde (5 g, 24.6 mmol), ethane-1,2-diol (4.12 ml, 73.9 mmol), and p-toluenesulfonic acid (424 mg, 2.46 mmol). The resulting mixture was placed under nitrogen, dissolved in anhydrous toluene (100 ml) and heated under reflux for 18 h. After cooling, the mixture was concentrated in vacuo. The residue was diluted with EtOAc (50 ml) and the organic phase was washed with sat. NaHCO3 solution (30 ml), brine (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (95:5) as the eluent to give the title compound (4.69 g, 77%). The structure was confirmed by 1H NMR.

출처