Reaktion #69521

Reaktionsgleichung

triethylamine

methanesulfonyl chloride

(4-bromo-3,5-dimethoxyphenyl)methanol

dichloromethane

→

title compound

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

Lösungsmittel

ethyl acetate

water

n-heptane ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a mixture of (4-bromo-3,5-dimethoxyphenyl)methanol (10.0 g, 40.6 mmol) and dichloromethane (100 mL) were added triethylamine (12.4 mL, 89.3 mmol) and methanesulfonyl chloride (3.46 mL, 44.7 mmol) in this order while cooling on ice, and the mixture was stirred at room temperature for 14 hours. To the mixture was added water, 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 (2.47 g, 9.30 mmol).

Quelle