تفاعل #69521

معادلة التفاعل

triethylamine

methanesulfonyl chloride

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

dichloromethane

→

title compound

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

المذيبات

ethyl acetate

water

n-heptane ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر