Reaktion #807944

Reaktionsgleichung

3-bromo-7-nitrodibenzothiophene-5-oxide

acetic acid

SnCl2.2H2O

→

7-bromodibenzothiophene-3-yl-amine

Lösungsmittel

hydrochloric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA flask equipped with a stirrer
2. 2
   workup.ADDITIONwas added dropwise at 14 to 18° C. over 1 hour
3. 3
   FiltrationThe resulting reactant was filtered
4. 4
   Waschenwashed with 1:1 glacial acetic acid/concentrated hydrochloric acid
5. 5
   ExtraktionThe reactant was extracted with ethyl acetate
6. 6
   Waschenwashed with water
7. 7
   Einengenconcentrated
8. 8
   Sonstigepurified by silica gel chromatography
9. 9
   workup.ADDITIONmixed with 0.1 wt % triethylamine as an eluting solvent

Vorschrift

A flask equipped with a stirrer and a thermometer was charged with 26.98 g of the intermediate 3-bromo-7-nitrodibenzothiophene-5-oxide prepared in Example 1-2 and 269.8 g of glacial acetic acid in a nitrogen atmosphere. 112.7 g of SnCl2.2H2O dissolved in 158 g of concentrated hydrochloric acid was added dropwise at 14 to 18° C. over 1 hour, and stirred overnight at room temperature. The resulting reactant was filtered, washed with 1:1 glacial acetic acid/concentrated hydrochloric acid, and neutralized with 1100 g of a 7 wt % aqueous solution of sodium hydroxide. The reactant was extracted with ethyl acetate, washed with water, concentrated, and purified by silica gel chromatography using 1:1 hexane/chloroform mixed with 0.1 wt % triethylamine as an eluting solvent, to thereby obtain 17.31 g of objective 7-bromodibenzothiophene-3-yl-amine. The product was subjected to elemental analysis, the results of which are as follows:

Quelle