Reaktion #699799

Reaktionsgleichung

4-bromo-3-methoxyphenol

K2CO3

isopropyl iodide

→

desired compound

1-Bromo-2-methoxy-4-(1-methylethoxy)benzene

Lösungsmittel

2-butanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture is heated
2. 2
   Temperaturunder reflux for 17 hours
3. 3
   Filtrationthen is filtered
4. 4
   Einengenconcentrated by evaporation of the solvent
5. 5
   SonstigeThe residue is partitioned between Et2O and H2O
6. 6
   ExtraktionThe Et2O layer is extracted with 5% NaOH (2×50 mL)
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over MgSO4
9. 9
   SonstigeThe solvent is evaporated
10. 10
    Sonstigethe resulting residue is purified by flash chromatography (5% EtOAc/hexane)

Vorschrift

To a stirred suspension of 4-bromo-3-methoxyphenol (2.03 g, 10 mmol) and K2CO3 (1.38 g, 10 mmol) in 2-butanone (70 mL) at ambient temperature under argon is added dropwise isopropyl iodide (2.21 g, 13.3 mmol). The resulting mixture is heated and stirred under reflux for 17 hours. The mixture is allowed to cool to ambient temperature then is filtered and concentrated by evaporation of the solvent. The residue is partitioned between Et2O and H2O. The Et2O layer is extracted with 5% NaOH (2×50 mL), washed with brine, and dried over MgSO4. The solvent is evaporated and the resulting residue is purified by flash chromatography (5% EtOAc/hexane) to afford the desired compound as a pale yellow oil. 2.13 g (87%).

Quelle