Reaktion #69522

Reaktionsgleichung

2-bromo-5-(chloromethyl)-1,3-dimethoxybenzene

DMF

cyclobutyl alcohol

DMF

sodium hydride

→

title compound

Ausbeute 85.4%

2-Bromo-5-[(cyclobutyloxy)methyl]-1,3-dimethoxybenzene

Ausbeute 85.4%

Lösungsmittel

ethyl acetate

n-heptane ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile cooling on ice
2. 2
   workup.ADDITIONTo the mixture was gradually added dropwise
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for one hour
4. 4
   Temperaturwhile cooling on ice
5. 5
   workup.STIRRINGAfter thoroughly shaking the mixture
6. 6
   Sonstigethe organic layer was separated
7. 7
   Waschenthe organic layer was washed with brine
8. 8
   Trocknendried over anhydrous magnesium sulfate
9. 9
   FiltrationThe mixture was filtered
10. 10
    workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

Vorschrift

To a mixture of cyclobutyl alcohol (4.16 g, 57.7 mmol) and DMF (30 mL) was added sodium hydride (60% oil dispersion: 2.31 g, 57.7 mmol) while cooling on ice, and the mixture was stirred at room temperature for one hour. To the mixture was gradually added dropwise a mixture of 2-bromo-5-(chloromethyl)-1,3-dimethoxybenzene (2.47 g, 9.3 mmol) and DMF (30 mL), and the mixture was stirred at room temperature for one hour. Water was added to the mixture while cooling on ice, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1) to obtain the title compound (2.39 g, 7.94 mmol).

Quelle