Reaktion #81683

Reaktionsgleichung

sodium sulfate

3-bromo-4-hydroxy-5-methoxybenzaldehyde

hydroxylammonium sulfate

1-chloronaphthalin

→

3-bromo-4-hydroxy-5-methoxybenzonitrile

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige2 hours
2. 2
   TemperaturThe reaction mixture is then cooled to 30° C.
3. 3
   workup.ADDITIONnitrogen is introduced until atmospheric pressure
4. 4
   workup.STIRRINGwhile further stirred
5. 5
   Filtrationfiltered
6. 6
   ExtraktionThe filter cake is extracted three times each with 2000 parts by weight of dichloromethane
7. 7
   Sonstigeevaporated to 1/3 of their volume
8. 8
   Sonstigethe next 17000 parts by weight are collected in one fraction
9. 9
   Sonstigeevaporated to dryness
10. 10
    Sonstigeis freed from traces of adsorbed 1-chloronaphthalin at 80° C. in the vacuum

Vorschrift

With stirring (20 rpm), a turbine dryer is charged at room temperature with 1280 parts by weight of anhydrous sodium sulfate, 462 parts by weight of 3-bromo-4-hydroxy-5-methoxybenzaldehyde, 172 parts by weight of hydroxylammonium sulfate and 298 parts by weight of 1-chloronaphthalin. Following evacuation to 70 mbar, the mixture is heated to 130° C. and kept at this temperature for 31/2 hours. The reaction mixture is then cooled to 30° C. and nitrogen is introduced until atmospheric pressure is reached. After 2650 parts by weight of dichloromethane are added, the suspension is kept for 20 min at room temperature while further stirred and then filtered. The filter cake is extracted three times each with 2000 parts by weight of dichloromethane. The solvent extracts are combined with the first filtrate and evaporated to 1/3 of their volume. The solution of the raw product in dichloromethane is subjected to column chromatography using 1400 parts by weight of silica gel 60 [70-230 mesh (Merck)] and 26500 parts by weight of dichloromethane as eluent. After a portion corresponding to the dead volume of the column is first discarded, the next 17000 parts by weight are collected in one fraction and evaporated to dryness. The residue is freed from traces of adsorbed 1-chloronaphthalin at 80° C. in the vacuum. 334.5 parts by weight of 3-bromo-4-hydroxy-5-methoxybenzonitrile are obtained with a purity of over 98% (TLC) and a melting point of 144°-145° C.

Quelle