Reaktion #1702075

Reaktionsgleichung

sodium borohydride

2-bromo-5-methoxybenzaldehyde

cyclopropylamine

toluene

→

crude product

N-(2-bromo-5-methoxybenzyl)cyclopropanamine

Lösungsmittel

water

methanol

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a flask fitted with a Dean-Stark trap
2. 2
   Temperaturat reflux for 4 hours
3. 3
   EinengenThe solution was then concentrated
4. 4
   Sonstigeto give a yellow oil to which
5. 5
   TemperaturThe reaction mixture was cooled on icebath
6. 6
   workup.ADDITIONAfter complete addition
7. 7
   workup.STIRRINGthe reaction mixture was stirred 2 hours at room temperature

Vorschrift

In a flask fitted with a Dean-Stark trap was introduced 2-bromo-5-methoxybenzaldehyde (5.68 g, 26.41 mmol), cyclopropylamine (3.02 g, 52.83 mmol) and toluene (70 ml). The reaction mixture was stirred at room temperature for 1 hour and then at reflux for 4 hours. The solution was then concentrated to give a yellow oil to which was added methanol (30 ml). The reaction mixture was cooled on icebath followed by portionwise addition of sodium borohydride (2.00 g, 52.83 mmol). After complete addition, the reaction mixture was stirred 2 hours at room temperature, and then water (70 ml) was added. The crude product was isolated by extraction with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered, and finally evaporated under reduced pressure.

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