Reaktion #8806

Reaktionsgleichung

sodium hydroxide

aluminum

sodium aluminate

isoquinoline

AlCl3

Bromine

→

solid

Ausbeute 26.0%

5-Bromoisoquinoline

Ausbeute 26.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a condenser
2. 2
   Sonstigeterminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle
3. 3
   TemperaturThe mixture was heated to 75–85° C
4. 4
   Sonstigeof 4 hours
5. 5
   workup.ADDITIONThe almost black mixture was poured
6. 6
   workup.STIRRINGinto vigorously hand-stirred
7. 7
   Extraktionthe oily layer was extracted with ether
8. 8
   TrocknenAfter being dried with Na2SO4
9. 9
   Einengenconcentrated
10. 10
    Extraktionthe ether extract
11. 11
    workup.DISTILLATIONwas distilled at about 0.3 mm

Vorschrift

The apparatus was a 500 mL three-necked flask equipped with a condenser, dropping funnel, and a stirrer terminating in a stiff, crescent-shaped Teflon polytetrafluroethylene paddle. To the isoquinoline (57.6 g, 447 mmol) in the flask was added AlCl3 (123 g, 920 mmol). The mixture was heated to 75–85° C. Bromine (48.0 g, 300 mmol) was added using a dropping funnel over a period of 4 hours. The resulting mixture was stirred for one hour at 75° C. The almost black mixture was poured into vigorously hand-stirred cracked ice. The cold mixture was treated with sodium hydroxide solution (10 N) to dissolve all the aluminum salts as sodium aluminate and the oily layer was extracted with ether. After being dried with Na2SO4 and concentrated, the ether extract was distilled at about 0.3 mm. A white solid (16.3 g, 78 mmol) from a fraction of about 125° C. was obtained (26% yield). The product was further purified by recrystallization (pentane or hexanes): mp 80–81° C.;

Quelle