反应 #5452

反应方程式

6-bromo-5-chlorovanillin

1.8-diazabicyclo[5,4,0]-7-undecene

methyl iodide

diisopropylethylamine

methyl iodide

→

title compound

收率 71.0%

2-Bromo-3-chloro-4,5-dimethoxybenzaldehyde

收率 71.0%

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度under cooling with ice
2. 2
   温度under cooling with ice
3. 3
   workup.STIRRINGthe mixture was stirred for 20 hours at room temperature
4. 4
   workup.DISTILLATIONAfter distilled off the solvent, 200 ml of dichloromethane
5. 5
   workup.ADDITIONwere added to the residue, which
6. 6
   洗涤was washed with water
7. 7
   干燥After dried over anhydrous magnesium sulfate
8. 8
   其他the concentrated residue was purified by means of silica gel column chromatography (hexane-AcOEt 5:1)

实验过程

Into 50 ml of acetonitrile were suspended 5.39 g (20.3 mmol), of 6-bromo-5-chlorovanillin, and 3.04 ml (20.3 mmol) of 1.8-diazabicyclo[5,4,0]-7-undecene and 2.53 ml (40.6 mmol) of methyl iodide were added dropwise under cooling with ice. After stirred for 5 hours at room temperature, 3.9 ml (22.33 mmol) if diisopropylethylamine and 2.53 ml (40.6 mmol) of methyl iodide were added under cooling with ice and the mixture was stirred for 20 hours at room temperature. After distilled off the solvent, 200 ml of dichloromethane were added to the residue, which was washed with water. After dried over anhydrous magnesium sulfate, the concentrated residue was purified by means of silica gel column chromatography (hexane-AcOEt 5:1) to obtain 4.04 g (yield 71%) of title compound as colorless needle-like crystals.

来源